There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 123-93-3 | MDL No. : | MFCD00004359 |
Formula : | C4H6O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UVZICZIVKIMRNE-UHFFFAOYSA-N |
M.W : | 150.15 | Pubchem ID : | 31277 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 32.48 |
TPSA : | 99.9 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.17 cm/s |
Log Po/w (iLOGP) : | 0.18 |
Log Po/w (XLOGP3) : | 0.06 |
Log Po/w (WLOGP) : | -0.11 |
Log Po/w (MLOGP) : | -0.54 |
Log Po/w (SILICOS-IT) : | -0.38 |
Consensus Log Po/w : | -0.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.54 |
Solubility : | 42.8 mg/ml ; 0.285 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.71 |
Solubility : | 2.92 mg/ml ; 0.0194 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.47 |
Solubility : | 444.0 mg/ml ; 2.96 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.56 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.7% | at 65℃; for 4 h; | Weigh 3.0 g of 2,2'-thiodiacetic acid in a 50 mL round bottom flask.15 mL of acetic anhydride was added.After refluxing at 65 ° C for 4 hours,Ethyl anhydride is distilled off under reduced pressure.Acetic acid, etc.; add appropriate amount of ether,Repeatedly steaming 2-3 times,Obtained a white solid powder,Dry at 40 ° C overnight,That is, 2,2'-thiodiacetic anhydride,The yield was 98.7percent. |
91% | With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3 h; Inert atmosphere; Reflux | General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. . |
78% | With trifluoroacetic anhydride In ethyl acetate at 20℃; for 24 h; | General procedure: To a stirring suspension of corresponding dicarboxylic acid in dry EtOAc (50 mL per 2 g) a solution of trifluoroacetic acid anhydride (2 equiv.) in dry EtOAc was added in one portion at room temperature. After 24 h the resulting solution was concentrated under reduced pressure, and the residue was thoroughly washed with cold petroleum ether (30 mL) to afford pure anhydride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid;Heating / reflux; | Example A:; [0078] Synthesis of 3,4-ethylenedioxythiophene methanol is adapted from the publication "Electropolymerization of and 3,4-ethylenedioxythiophene methanol in the presence of dodecylbenzenesulfonate", Lima A, Schottland P, Sadki A, Chevrot C; Synth. Met. 1998, 93, 33-41.; 1) Synthesis of diethyl thiodiglycolate; [0079] In a 2-necked round bottom flask equipped with a reflux condenser and an equilibrium addition funnel 100 g (0.667 mol) thiodiglycolic acid was dissolved in 500 mL refluxing ethanol. The equilibrium addition funnel was charged with 40 mL concentrated sulfuric acid. The acid was added dropwise EPO <DP n="24"/>and the reaction refluxed overnight. Upon cooling the reaction to room temperature it was carefully poured into 600 mL water. The product was extracted with diethyl ether until the ether wash no longer contained the desired product. The organic extracts were washed with a saturated sodium bicarbonate solution three times. Upon drying with magnesium sulfate and solvent removal under reduced pressure a colorless oil was isolated (131 3 g, 95% yield). Structure and pu?ty were confirmed by 1YU13C NMR and GC-MS. |
95.1% | With sulfuric acid; at 86℃; for 0.333333h;Microwave irradiation; | General procedure: Example A1 15.015 g of 2,2'-thiodiacetic acid (Acros, Belgium), 55.284 g of ethanol (ECHO, Taiwan), and 4.9 g of sulfuric acid (Sigma-Aldrich, Switzerland) were added into 20 g of toluene (ECHO, Taiwan) and then stirred for mixing and dissolving the reagents above. The obtained solution was moved into a microwave reactor and heated by a 2.45 GHz microwave at a power of 500 W for 30 minutes. A Dean-Stark receiver was installed outside the microwave reactor for dehydrating. The temperature of the heated solution was 86 - 87 C and refluxed. The solution was cooled down after the reaction, and then its pH value was adjusted to 7.0 - 7.5 by adding NaOH(aq) in order to stop esterification. The solution was then extracted by ethyl acetate/ n-hexane (9/1) and saturated salt water for three times. The obtained organic layer was dried by anhydrous magnesium sulfate, filtered, evaporated to remove solvent, and then vacuumed under a reduced pressure to obtain 17.1 g diethyl thioglycolate. The yield is 83.0%. |
79% | sulfuric acid; for 12h;Heating / reflux; | Carboxylic acid EDOT monomer can be synthesized, as shown in Scheme 1. Products formed and reacted are designated by Arabic numerals. First thiodiglycolic acid (1 , 25 g, 0.17 mol) is refluxed with 10 ml sulfuric acid in 100 ml ethanol for 12 hours. The solution is cooled, diluted with 150 ml of water, and the product is extracted into diethyl ether three times. The organic layer is then washed three times with Na2CO3ZH2O, dried with MgSO4 and the solvent is removed to produce 27.06 g of diethyl thiodiglycolate (2, 79% yield ). Diethyl thioglycolate (27.06 g, 0.13 mol) is then added dropwise with diethyl oxalate (50 g, 0.34 mol) to 250 ml of sodium ethoxide (0.58 mol) at 0 C. After complete addition the solution is refluxed for 1 hour to form diethyl 3,4- dihydroxythiophene-2,5-dicarboxylate disodium salt (3). After filtration, (3) is acidified using hydrochloric acid, and the precipitate is filtered and washed with water. The product, diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate (4), is dried and recrystallized in methanol to produce a yield of 27.02 g (80 %). Next, (4) (8.75g, 0.034 mol) is added to 200 ml of boiling ethanol. Epibromohydrin (3.75 ml, 0.045 mol) and K2CO3 (0.94 g in 50 ml water) are added to the reaction. After 30 minutes, more epibromohydrin (6.5 ml, 0.079 mol) and K2CO3 (0.5 g) are added and the solution is refluxed for 60 hours. The product is diluted with 150 ml of acidified water (5 % HCI) and extracted two times with chloroform. The organic layer is then washed with 5 % aqueous KCI, dried with MgSO4, and the solvent is evaporated. The product, diethyl 2-(hydroxymethyl)-2,3- dihydrothieno[3,4-b] [1 ,4]dioxin-5,7-dicarboxylate (5) is purified by precipitation in diethyl ether. The by-product, diethyl 2-hydroxy-2,3-dihydrothieno[3,4- b][1 ,4]dioxin-5,7-dicarboxylate, is also present with (5) but this compound cannot react in the next step so it is not separated from (5). Oxidation of the hydroxyl group on (5) is achieved by adding a catalytic amount of pyridinium chlorochromate (0.18 g, 0.8 mmol) and (5) (8.54 g, mixture with by-product) to a cooled solution (0 0C) of periodic acid (15 g, 0.066 mol) in 240 ml of acetonitrile. The solution is stirred for 3 hours as it warms to room temperature. After the reaction, the solution is diluted with 300 ml of ethyl acetate, washed with a 1 :1 solution of brine:water, and the product is extracted into a solution of sodium bicarbonate and water. The aqueous later is then acidified with HCI and the <n="11"/>product is extracted into ethyl acetate. The organic layer is then dried with MgSO4 and the solvent is removed. The product, diethyl 2-(carboxylic acid)-2,' - dihydrothieno[3,4-b] [1 ,4] dioxin-5,7 dicarboxylate (6), is recrystallized in xylenes to produce a 26 % yield from compound (4) to compound (6). Compound (6) (2,8g) is then reacted with KOH (3g, 0.05 mol) in 75 ml of water and 30 ml of ethanol for 1 hour at 60 C. After the reaction the solvent is removed and the product is washed with ethanol. The product is then filtered, dissolved in 150 ml of water and acidified with HCI. The product, diethyl 2-(carboxylic acid)-2,3- dihydrothieno[3,4-b] [1 ,4]dioxin-5,7-dicarboxylic acid (7), is recovered as a white precipitate after stirring in acidified water for 3 hours in -100% yield (2.36 g, 8.6 mmol). Compound (7) (2.36 g) is decarboxylated by refluxing with copper chromite catalyst (0.24 g, 0.76 mmol) in 14 ml of freshly distilled quinoline at 160 - 170 C for 2 hours. The solution is diluted with ethyl acetate and filtered to remove catalyst. The product is then washed with 5 % HCI three times, NaCI/water twice and extracted into 2 % KOH. The aqueous layer is then acidified with HCI and the product is extracted into ethyl acetate, dried with MgSO4 and the solvent is removed to produce 1.17 g (75% yield) of the final product, 2,3-dihydrothieno[3,4-b][1 ,4]dioxin-2-carboxylic acid i.e. carboxylic acid EDOT (8). This reaction scheme results in a total yield from compound 1 to compound 8 of 12%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.7% | With acetic anhydride; at 65℃; for 4h; | Weigh 3.0 g of 2,2'-thiodiacetic acid in a 50 mL round bottom flask.15 mL of acetic anhydride was added.After refluxing at 65 C for 4 hours,Ethyl anhydride is distilled off under reduced pressure.Acetic acid, etc.; add appropriate amount of ether,Repeatedly steaming 2-3 times,Obtained a white solid powder,Dry at 40 C overnight,That is, 2,2'-thiodiacetic anhydride,The yield was 98.7%. |
91% | With oxalyl dichloride; N,N-dimethyl-formamide; In toluene; for 3h;Inert atmosphere; Reflux; | General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. . |
78% | With trifluoroacetic anhydride; In ethyl acetate; at 20℃; for 24h; | General procedure: To a stirring suspension of corresponding dicarboxylic acid in dry EtOAc (50 mL per 2 g) a solution of trifluoroacetic acid anhydride (2 equiv.) in dry EtOAc was added in one portion at room temperature. After 24 h the resulting solution was concentrated under reduced pressure, and the residue was thoroughly washed with cold petroleum ether (30 mL) to afford pure anhydride. |
With acetic anhydride; In tetrahydrofuran; for 1.5h;Reflux; | (i) [(2-([4-Chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethyl)sulfanyl]acetic acid The mixture containing 5.0 g (33.3 mmol) of 2,2'-thiodiglycolic acid and 30 mL of acetic anhydride were heated under reflux for 1.5 hours. The reaction solution was condensed, thereby quantitatively giving 2,2'-thiodiglycolic anhydride 3.78 g (28.8 mmol) of the 2,2'-thiodiglycolic anhydride and 5.35 g (28.8 mmol) of 2-amino-5-chlorobenzoic acid methyl were heated under reflux in 50 mL of THF for 4 hours. The reaction mixture was condensed, and IPE was added to the resulting crystals. The mixture was then filtered, thereby giving 8.57 g of [(2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethyl)sulfanyl]acetic acid (yield: 93%). 1H-NMR (DMSO-d6) delta: 3.38 (2H, s), 3.56 (2H, s), 3.88 (3H, s), 7.68 (1H, dd, J =9.0, 2.7 Hz), 7.87(1H, d, J= 2.7 Hz), 8.33 (1H, d, J = 9.0 Hz), 11.1 (1H, s), 12.7 (1H, br). | |
With phosphorus trichloride; In chloroform; at 55℃; for 2h;Heating / reflux; | Thiodiglycolic anhydride was prepared according to the method of Morril et al., J. Org. Chem., 26, 4103 (1961). Thiodiglycolic acid (32.4 g, 0.216 mol) and phosphorous trichloride (9.2 g, 5.5ml, 0.065 mol) were stirred at 55C in chloroform (40 ml) until no HCl gas evolution ceased. The mixture was then heated at reflux for 1 hour, after which an additional amount (4.6 g, 2.9 ml, 0.033 mol) of phosphorous trichloride was added. After the addition, an oil precipitated and refluxing was continued for an additional 1 hour. The hot chloroform solution was then decanted away from the oil and set aside to cool. A white crystalline solid was deposited, which was filtered and dried (24.6 g). A TLC (SiO2, chloroform/methanol 4:1) showed one major component, plus a very small amount of the starting di-acid. A solution of buprenorphine (6.8 g, 0.0146 mol) and thiodiglycolic anhydride (11.6 g, 0.088 mol) in a 3:5 mixture of dry ethe?acetonitrile (160 ml) was stirred at room temperature for 6 hours. An oil precipitated and stirring was stopped. The mixture was allowed to stand for 48 hours. A white solid formed, which was filtered off and dissolved in hot methanol (25 ml). Dry ether (500ml) was added followed by ethereal HCl. A white solid precipitated (6.4 g). A 2.5 g portion of this was re-crystallized from methanol/ether to give the desired buprenorphine hemi-dithioglycolate hydrochloride monohydrate (2.Ig), melting point 225-226C (decomp.). Found (percent) C, 60.50; H, 7.30; N, 2.03: C33H45NO7S(HCl)(H2O) requires C, 60.57; H, 7.39; N, 2.14; 3300 (OH), 1745, and 1710 in cm"1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.0833333h;Sonication; | General procedure: For the fabrication of sulfoxide, 1 mmol sulfide, 0.6 ml H2O2 (33%) and 0.005 g nanocatalyst were stirred at room temperature. Also, for producing disulfides, 1 mmol thiols and 0.4 ml H2O2 (33%) with 0.008 g nanocatalyst in ethanol as a green solvent were mixed at 25 C. After completion of the reaction, the catalyst was removed by a magnet and the product was extracted with ethyl acetate and dried using a vacuum dryer. |
With perchloric acid; tris(2,2'-bipyridine)iron(III) perchlorate; sodium perchlorate; water; at 30℃;Kinetics; Mechanism; | All kinetic measurements were performed under pseudo firstorder conditions where [TDGA] was always in excess over[Fe(bpy)3]3+, in perchloric acid medium at a constant temperatureof 30.0 ± 0.05C, unless stated. The ionic strength of the medium was maintained by adding sodium perchlorate solution.Requisite quantities of TDGA, sodium perchlorate, perchloric acid and other reagents were thermostated in a reaction vessel.Tris(2,2'-bipyridine)iron(III) separately equilibrated was transferred to the reaction vessel at zero time and shaken well to initiate the reaction. The molar extinction coefficients of [Fe(bpy)3]2+ and[Fe(bpy)3]3+ are 8650 and 320 respectively at the wavelength regions 524 and 618 nm [24,25]. Since the molar extinction coefficient for the Fe(II) complex is higher than Fe(III) complex, the rate of formation of [Fe(bpy)3]2+ complex was followed using the UV-vis spectrophotometer by measuring the increase in the absorbance at wavelength 524 nm. The reaction was followed at definite time intervals till maximum absorbance (A1) was reached. The increase in the absorbance of [Fe(bpy)3]2+ with time shows the progress of the reaction. In some cases duplicate runs were carried out to ensure the reproducibility. | |
With dihydrogen peroxide; In acetic acid; | General procedure: The commercially available sulfides were generously donated by Evans Chemicals, Inc.9 The sulfoxides and sulfones were prepared according to published procedures10 via stepwise hydrogen peroxide oxidation of the corresponding sulfides in glacial acetic acid. The products were purified through recrystallization from a 1:3 ethyl acetate/benzene solution, or, in the case of long chain acids, from water. All melting points agreed with published values. All melting points agreed with published values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In ethyl acetate; at 0℃; for 7.5h;Inert atmosphere; Reflux; | The macrocyclic ligand, TTDD was prepared by followingthe same procedure as employed for the synthesis of oxamacrocyclicligand, OTDD except using 2, 20-thiodiaceticacid in place of 2, 20-oxydiacetic acid (Fig. 2). Thionyl chloride (6.52 mL, 90 mmol) was added slowly toa solution of 2, 20-oxydiacetic acid (2.01 g, 15 mmol) inethyl acetate (30 mL) at 0-5 C under nitrogen atmosphere. The reaction mixture was stirred for 30 min at0-5 C and at room temperature for the same durationfollowed by refluxing along with stirring at 70 C over aperiod of 7 h. The highly hygroscopic and reactive compound(2, 20-oxydiacetyl chloride) yielded by concentratingthe solution under reduced pressure (Scheme 1). Both 2, 20-oxydiacetyl chloride (2 g, 11.6 mmol) and 1,5-diamino-3-aza-pentane (1.29 mL, 12 mmol) were diluted by addingdry THF (120 mL) separately and added drop wisesimultaneously by dropping funnels to ice cooled dry THF(350 mL) under nitrogen-atmosphere. During drop wiseaddition of these reactants, triethylamine (5.02 mL,36 mmol) was added to catalyze the reaction. The reactionmixture was stirred at 0-5 C followed by overnight stirringat room temperature. Progress of reaction was monitoredby TLC. Solvent was removed under reducedpressure to yield the macrocyclic product OTDD, whichwas purified by washing with chloroform (5 mL) 8-10times followed by etheration and vacuum drying to yieldthe pure compound (Fig. 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of 0.2 M monochloroacetic acid in 30 mL of water was prepared. To the above solution 0.2 M of sodium bicarbonate was added in small portions with constant stirring until the solution become neutral. The mixture was allowed to cool in an icebath. To the above mixture 0.12 M of hydrated sodium sulphide dissolved in 37 mL of water was added slowly with constant stirringby maintaining 25-30C. The reaction mixture was cooled in the ice bath for an hour. To this mixture 15 mL of concentrated sulphuric acid was added with stirring at room temperature. TDGA was obtained by extraction and evaporation of the ether layer in a rotary vacuum evaporator.TDGA was recrystallized using ethyl acetate and benzene mixture.The purity was obtained from the melting point. The meltingpoint observed was 129 ± 1C at 1 atm was reported by Barkenbusand Landis as 129-130C [22]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.3% | With hydrogenchloride; In water; for 72h;Reflux; | The ligand was prepared according to Matthews et al. [45]. Thiodiacetic acid (15.02 g, 100 mmol)and o-phenylenediamine (21.63 g, 200 mmol) were mixed in a solution of 18% HCl (230 mL). Thesolution was heated under reflux 3 d. A green precipitate formed after cooling was dissolved afteraddition of water (500 mL). The solution was stirred and ammonia (28%) was added until the pH of thesolution became 9. During the addition of ammonia, a light brown precipitate was obtained. The precipitatewas collected on a frit, washed several times with water and dried at 40 C. Yield: 32.3%. Anal. Calcd.for tbb·3/2H2O: C, 59.8; H, 5.3; N, 17.4; S, 10.0. Found: C, 60.1; H, 5.2; N, 17.2; S, 9.8%. IR (cm-1):437w, 736vs, 844w, 1027m, 1129w, 1159m, 1226m, 1273s, 1313m, 1440vs, 1454s, 1535m, 1625w,2784m, 2939s, 3059s, 3377m. UV-Vis (MeOH/nm): 290, 322, 340. |
In hydrogenchloride; | EXAMPLE 113 2-[(1H-benzimidazol-2-ylmethyl)thio]methyl}-1H-benzimidazole A solution of 4.1 g (27.3 mmol) <strong>[123-93-3]thiodiacetic acid</strong> and 4.9 g (27.3 mmol) o-phenylene diamine in 40 ml 4N HCl was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature an neutralised with conc. NH4OH. The formed precipitate was filtered, washed with water (3*40 ml) and dried under vacuum. Yield-2.4g (25.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With hydrogenchloride In water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With sodium hydroxide; In water; at 120℃; for 48h;High pressure; | General procedure: A mixture of Pb(NO3)2 (66.2 mg, 0.2 mmol), H2L (30.0 mg, 0.2 mmol), NaOH (5 M) 0.3 mL and H2O (10 mL) were placed in a 25 mL Teflon-lined steel vessel and heated to 120 C for 2 days, and then cooled to room temperature over the period of 72 h. The resulting colorless block-shaped crystals of 1 were washed several times by water and diethyl ether. The yield is 23% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.77; H, 1.43%. 2 was prepared in a similar manner as that of 1 only by changing the hydrothermal reaction temperature from 120 C to 170 C. The resulting colorless needle-shaped crystals of 2 were washed several times by water and diethyl ether. The yield is 28% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.68; H, 1.24%. 3 was also prepared in a similar manner as that of 1 only by using PbCl2 (55.6 mg, 0.2 mmol) instead of Pb(NO3)2. The resulting colorless plate-shaped crystals of 3 were washed several times by water and diethyl ether. The yield is 24% based on Pb. Anal. Calc. for C8H8Cl2O8Pb3S2: C, 9.72; H, 0.82%. Found: C, 9.87; H, 1.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With sodium hydroxide; In water; at 170℃; for 48h;High pressure; | General procedure: A mixture of Pb(NO3)2 (66.2 mg, 0.2 mmol), H2L (30.0 mg, 0.2 mmol), NaOH (5 M) 0.3 mL and H2O (10 mL) were placed in a 25 mL Teflon-lined steel vessel and heated to 120 C for 2 days, and then cooled to room temperature over the period of 72 h. The resulting colorless block-shaped crystals of 1 were washed several times by water and diethyl ether. The yield is 23% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.77; H, 1.43%. 2 was prepared in a similar manner as that of 1 only by changing the hydrothermal reaction temperature from 120 C to 170 C. The resulting colorless needle-shaped crystals of 2 were washed several times by water and diethyl ether. The yield is 28% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.68; H, 1.24%. 3 was also prepared in a similar manner as that of 1 only by using PbCl2 (55.6 mg, 0.2 mmol) instead of Pb(NO3)2. The resulting colorless plate-shaped crystals of 3 were washed several times by water and diethyl ether. The yield is 24% based on Pb. Anal. Calc. for C8H8Cl2O8Pb3S2: C, 9.72; H, 0.82%. Found: C, 9.87; H, 1.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With sodium hydroxide; In water; at 120℃; for 48h;High pressure; | General procedure: A mixture of Pb(NO3)2 (66.2 mg, 0.2 mmol), H2L (30.0 mg, 0.2 mmol), NaOH (5 M) 0.3 mL and H2O (10 mL) were placed in a 25 mL Teflon-lined steel vessel and heated to 120 C for 2 days, and then cooled to room temperature over the period of 72 h. The resulting colorless block-shaped crystals of 1 were washed several times by water and diethyl ether. The yield is 23% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.77; H, 1.43%. 2 was prepared in a similar manner as that of 1 only by changing the hydrothermal reaction temperature from 120 C to 170 C. The resulting colorless needle-shaped crystals of 2 were washed several times by water and diethyl ether. The yield is 28% based on Pb. Anal. Calc. for C8H8O8S2Pb2: C, 13.52; H, 1.13%. Found: C, 13.68; H, 1.24%. 3 was also prepared in a similar manner as that of 1 only by using PbCl2 (55.6 mg, 0.2 mmol) instead of Pb(NO3)2. The resulting colorless plate-shaped crystals of 3 were washed several times by water and diethyl ether. The yield is 24% based on Pb. Anal. Calc. for C8H8Cl2O8Pb3S2: C, 9.72; H, 0.82%. Found: C, 9.87; H, 1.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid;pH 2.5; | General procedure: Compounds 1 and 2 were co-crystallized by combining 1.5ml of a 0.2M acetic acid with 0.75mL of a 0.2M uranyl nitrate and 0.75mL of a 0.2M tdg solution in a glass scintillation vial. The pH was adjusted to 3.0 by adding pyridine and crystals formed after 48h of slow evaporation. Compound 2 could also be synthesized in pure yields by combining equal aliquots of 0.2M UO2(NO3)2·6H2O and H2tdg, followed by an adjustment of the solution pH to 2.5 with pyridine. Crystals of 3 were synthesized in a similar manner as compound 2, but crystallization was induced by liquid-liquid diffusion with toluene. Crystals for each compound were filtered, washed with methanol and air dried. Yields for each of the final products were calculated as 5-10%, 85%, and 65% based upon U for compounds 1, 2, and 3, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic acid;pH 2.5; | General procedure: Compounds 1 and 2 were co-crystallized by combining 1.5ml of a 0.2M acetic acid with 0.75mL of a 0.2M uranyl nitrate and 0.75mL of a 0.2M tdg solution in a glass scintillation vial. The pH was adjusted to 3.0 by adding pyridine and crystals formed after 48h of slow evaporation. Compound 2 could also be synthesized in pure yields by combining equal aliquots of 0.2M UO2(NO3)2·6H2O and H2tdg, followed by an adjustment of the solution pH to 2.5 with pyridine. Crystals of 3 were synthesized in a similar manner as compound 2, but crystallization was induced by liquid-liquid diffusion with toluene. Crystals for each compound were filtered, washed with methanol and air dried. Yields for each of the final products were calculated as 5-10%, 85%, and 65% based upon U for compounds 1, 2, and 3, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 48h; | General procedure: To dry dichloromethane (80 mL), 2,2-diaminodiphenyl disulfide (2 mmol, 0.50 g),diacid (2 mmol), DCC (5 mmol, 1.30 g), triethylamine (5 mmol, 0.70 mL), and DMAP(catalytic) were added. The reaction mixture was stirred at room temperature for 48 h and filtered. To the filtrate, water was added and the resulting mixture was extracted with dichloromethane (3 × 50 mL). The combined organic layers were washed with dilute hydrochloric acid (2 × 50 mL) and water (2 × 50 mL), respectively. The resulting organic layer was dried using sodium sulfate and evaporated to afford crude product, whichwas purified via dry flash chromatography using ethyl acetate/methanol as the eluent for obtaining pure aza thia crowns as the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With sodium hydroxide; In water; at 170℃; for 48h; | A mixture of PbBr2 (73.4 mg, 0.2 mmol), H2L (30.0 mg,0.2 mmol), NaOH (5 M) 0.3 mL and H2O (10 mL) were placedin a 25 mL Teflon-lined steel vessel and heated to 170C fortwo days, and then cooled to room temperature over the periodof 72 h. The resulting colorless block-shaped crystals of 1 werewashed several times by water and diethyl ether. The yield is27% based on Pb. Anal. Calcd. for C8H8Br2O8Pb3S2: C, 8.92;H, 0.74%. Found: C, 9.11; H, 0.95%. FT-IR (KBr, cm-1): 1596 s,1421 s, 1388 m, 1140 m, 1128 m, 836 w, 702 m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15.3% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 30℃; for 60h; | (Step 1) A solution of 4-aminobenzonitrile (500 mg, 4.23 mmol), 2,2'-<strong>[123-93-3]thiodiacetic acid</strong> (3.18 g, 21.2 mmol), WSC (4.87 g, 25.4 mmol), DMAP (258 mg, 0.21 mmol) and DIEA (5.47 g, 42.3 mmol) in THF (200 mL) was stirred at room temperature for 60 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to give 2-((2-((4-cyanophenyl)amino)-2-oxoethyl)thio)acetic acid (162 mg, 15.3%) as a pale-yellow powder. 1H-NMR (300MHz, DMSO-d6) : delta3.42(2H,s), 3.47(2H,s), 7.75(2H,d,J=9.0Hz), 7.78(2H,d,J=9.0Hz), 10.53(1H,s), 12.64(1H,s), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | The ligand pmdien (0.2 ml, 1 mmol) was added to a stirred solutionof Ni(ClO4)2*6H2O (0.36 g, 1 mmol) in methanol (35 ml). The colour of solution turned to violet. Solution of tdaH2 (0.075 g,0.5 mmol) neutralized with KOH (0.056 g, 1 mmol) in water (5 ml) was added. Violet colour turned to green and after a while white precipitate was formed. Precipitate was removed by filtration and filtrate was left for crystallization. After a week green crystals (suitable for X-ray analyses) were collected on a frit funnel, washed with methanol and dried in air. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; | General procedure: To a well stirred solution of the corresponding 4-(sub:-1Hbenzo[d]imidazol-2-yl)aniline/4-(3H-imidazo[4,5-b]pyridin-2-yl)aniline (3a-f) (1 equiv) and triethylamine (2.5 equiv) indichloromethane was added the appropriate dicarboxylic acid(1 equiv) followed by propylphosphonic anhydride solution(2.5 equiv; 50% solution in ethyl acetate) at 0 C. The reactionmixture was warmed to room temperature and stirred at roomtemperature for 8h (monitored by TLC and LCMS for completion).The reaction mixture was then washed with water, brine driedover anhydrous sodium sulfate and concentrated under reducedpressure. The residue obtained was then purified by flash chromatographyto afford the desired product in good yield and purity asdescribed below.. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h; | To a solution of Docetaxel (0.4 g, 0.5 mmol) in DCM (100 mL) was added 2,2' -<strong>[123-93-3]thiodiacetic acid</strong> (0.075 g, 0.5 mmol), DMAP (0.075 g, 0.6 mmol), and EDC (0.19 g, 1.0 mmol). The reaction was stirred at room temperature for 16 hrs. The solution was concentrated and column chromatography gave Docetaxel 2'-carboxylic acid (0.26 g, 54%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In methanol; N,N-dimethyl-formamide; for 0.5h;Inert atmosphere; | The [Mo202S4(DMF)3] (0.5 g, 0.87 mmol) was suspended in 40 ml distilled and degassed DMF under argon. To this solution was added a mixture of 2,2 ' - <strong>[123-93-3]thiodiacetic acid</strong> (0.13 g, 0.87 mmol) and lBuOK (0.2g, 1.75 mmol) in dry methanol under argon. The resulting solution was stirred 30 minutes, the solvent removed in vacuo, and the dark red solid washed with ethanol and ether. The residue was redissolved in 50 ml dry DMF, filtered and precipitated with isopropanol. The dark red solid was isolated by filtration and dried in vacuum. Yield 0.27 g (60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With iodine; In methanol; N,N-dimethyl-formamide; for 2h; | The (Et4N)2[Mo202S8] (0,5 g, 0.67 mmol) was suspended in 40 ml DMF. To this solution was added iodine (0,17 g, 0,67 mmol) dissolved in 25 ml DMF. After the iodine addition was complete, a mixture of sodium carbonate (0,14 g, 1.34 mmol) and 2,2 ' -<strong>[123-93-3]thiodiacetic acid</strong> (0,10 g, 0.67 mmol) in 12 ml methanol was added. The resulting solution was stirred 2 hours, filtered, and the solvent removed in vacuum. The solid obtained was washed with alcohol, redissolved in 30 ml dry DMF, filtered and precipitated with ether. The dark red solid was isolated by filtration and dried in vacuo. Yield 0.19 g (50%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.7% | In water; at 30℃; for 1h; | An aqueous solution of Ce(NO3)3.6H2O (217mg, 0.5mmol) in water (5ml) was added to a solution of 2,2?-<strong>[123-93-3]thiodiacetic acid</strong> (150mg, 1mmol) in water (5ml) and piperazine (86mg, 1mmol) in water (5ml) under stirring in a 1:2:2M ratio, as shown in Scheme 1. The solution was heated very slightly (30C) for 1h. After 10days, plane, colorless crystals of the complex were obtained by slow evaporation of the solvent at room temperature. Yield 68.7%; M.p. (231-235)C. Anal. Calc. for C20H33Ce2N2O19S4: C, 23.18; H, 3.50; N, 2.73; S, 12.33. Found: C, 23.26; H, 3.49; N, 2.71; S, 12.40%. 1H NMR (D2O): delta H 3.44ppm (s, Hmethylene, tda2-), delta H 4.72ppm (s, HAmine, pipH22+), delta H 2.64ppm (s, Hmethylene, pipH22+); 13C NMR (D2O): delta C 183.90ppm (s, Ccarboxylate, tda2-), delta C 37.30ppm (s, Cmethylene, tda2-), delta C 40.29ppm (s, Cmethylene, pipH22+); UV-Vis (aqueous solution) (lambda, nm): 205 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.3% | In water; at 30℃; for 1h; | General procedure: An aqueous solution of Ce(NO3)3.6H2O (217mg, 0.5mmol) in water (5ml) was added to a solution of 2,2?-<strong>[123-93-3]thiodiacetic acid</strong> (150mg, 1mmol) in water (5ml) and piperazine (86mg, 1mmol) in water (5ml) under stirring in a 1:2:2M ratio, as shown in Scheme 1. The solution was heated very slightly (30C) for 1h. After 10days, plane, colorless crystals of the complex were obtained by slow evaporation of the solvent at room temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.6% | In water; at 20℃; for 1h; | General procedure: An aqueous solution of Ce(NO3)3.6H2O (217mg, 0.5mmol) in water (5ml) was added to a solution of 2,2?-<strong>[123-93-3]thiodiacetic acid</strong> (150mg, 1mmol) in water (5ml) and piperazine (86mg, 1mmol) in water (5ml) under stirring in a 1:2:2M ratio, as shown in Scheme 1. The solution was heated very slightly (30C) for 1h. After 10days, plane, colorless crystals of the complex were obtained by slow evaporation of the solvent at room temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 80℃; for 2h;Inert atmosphere; | Example III-10 Under the protective atomosphere of nitrogen gas, to a 250ml four-necked flask equiped with a stirrer, a thermometer,a condensing tube and a dropping funnel, there were added 6.19g (26mmol) 2,6-di-tert-butyl-4-mercaptophenol,16.38g (92mmol) thiodipropionic acid, 3.84g (17mmol) N-isopropyl-N?-phenyl p-phenylene diamine and 150mLtoluene, rapidly stirred, reacted at 80 degrees Celsius for 2h. Upon completion of the reaction, the solvent and water(generated during the reaction) were removed by vacuum distillation, the titled hindered phenol compound was obtainedby using column chromatography. The compound was characterized as follows : 1H NMR (300MHz, CDCl3) : delta 1.19 (6H), 1.36 (18H), 3.74 (1 H), 3.94 (2H), 3.96 (2H), 5.32 (1H), 6.80-7.26 (11 H),7.55 (1H); 13C NMR (75MHz, CDCl3) : delta 20.6, 29.6, 34.6, 34.7, 41.9, 48.2, 116.6, 119.3, 121.8, 126.2, 129.5, 136.5, 139.6,142.8, 146.1, 153.5, 166.2, 189.8; C33H42N2O3S2 (calculated) : C 68.48, H 7.31, N 4.84, O 8.29, S 11.08; (measured): C 68.41, H 7.28, N 4.91, 0 8.30,S 11. 11. | |
In toluene; at 80℃; for 2h;Inert atmosphere; | Under nitrogen atmosphere, a 250ml four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel was added 6.19 g (26mmol) 2,6-di-tert-butyl-4-mercaptophenol, 16.38 g (92mmol) thiodipropionic acid, 3.84 g (17mmol) N-isopropyl-N'-phenyl-p-phenylenediamine and 150mL of toluene, stirred rapidly for 2h at 80 deg. C. After completion of the reaction, the solvent was evaporated under reduced pressure and a small amount of water produced, purified by column chromatography to obtain the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.08% | In ethanol; water; at 150℃; for 36h;High pressure; | General procedure: The same synthetic method as that for 1 was used except thatH2atibdc was replaced by 2,2?-H2tda (0.025 g, 0.1 mmol). Colorlessblock crystals of 3 were isolated by washing with mother liquorand dried in air. The yield was 39.08% based on Zn. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With sodium hydrogencarbonate; In water; for 2h;Reflux; | To a solution of 1.5 g, 0.01 mol, of S(CH2COOH)2 in 30 ml H2O,neutralized with NaHCO3, was slowly added a neutralized solutionof 0.94 g, 0.01 mol, of CICH2COOH, also in 30 ml H2O. The reactionmixture was refluxed for 2 h. After cooling the solution was acidifiedto pH ~1 with sulphuric acid. The solvent was then removed invacuum and the residue washed with some cold water. A yield of0.44 g, 21%, of colourless crystals, suitable for the X-ray study, wasobtained from one crystallization fromwater. mp 176 C. 1H NMR inDMSO-d6, 600 MHz, 4.30 ppm (s); 13C NMR in H2O (with D2O as lock signal); 44.1 (s), 168.2 (s) ppm. FTIR (KBr), cm1, C 0: ~1790(sh), 1731 (s), 1654(w), 1396(s); CeS: 757, 687. MS (m/e) for 32S:208(Mw) < 1%, 164(eCO2) 6%, 150(eCH2COO) 7%, 132 (eCH2COO,H2O) 10%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: A mixture of Cu(OAc)2·2H2O (1.0mmol, 0.20g) and 2,2?-iminodiacetic acid (1.0mmol, 0.131g) were stirred in water at 70C for 30min and then nicotinamide (2.0mmol, 0.24g) in methanol (5.0mL) was added to the mixture. The obtained solution was stirred at 70C for 2h. After 2h, the resulting blue solution was filtered and evaporated at room temperature. Blue crystals of 1 were obtained one week later. Yield: 0.28g, 83% (based on Cu(OAc)2·2H2O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90mg | 10354] The reaction vessel was substituted by argon, 6-hy- droxy-3-(1 8-[4-hydroxy-2,6,6-trimethyl-3-oxo- 1 -cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17- nonaenyl)-2,4,4-trimethyl-2-cyclohexene- 1-one (astaxanthin, 2.00 g), 2,2?-<strong>[123-93-3]thiodiacetic acid</strong> (5.03 g), N,Ndiisopropylethylamine (8.66 g), 4-(N,N-dimethylamino) pyridine (0.82 g) and methylene chloride (60 mL) were mixed and the reaction solution was stirred for 18 hours at room temperature. 1 -Ethyl-3-(3-dimethyl-aminopropyl)car- bodiimide hydrochloride (6.42 g) was added to the reaction solution and the reaction solution was stirred further for 1 .5 hours. Completion of the reaction was confirmed by high performance liquid chromatography (HPLC) and polyacrylic acid (AQUALIC HL415 (NIPPON SHOKUBAI CO., LTD.), 60 mL) was added to the reaction solution. The reaction solution was stirred for 10 minutes and further polyacrylic acid (AQUALIC AS (NIPPON SHOKUBAI CO., LTD.), 10 g) was added thereto. Solidification of polyacrylic acid was confirmed, and the organic layer was isolated by decantation and filtration, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by reverse phase (ODS) column chromatography (10% CH2C12-MeOH:water=8:2 to 9:1) once and purified by the chromatography (10% CH2C12-MeOH:wa- ter=8:2 to 19:1) twice, and the fractions containing the product were dried under reduced pressure. To the purified product, CH2C12 (50 mL) and 1N-HC1 (50 mL) were added and the CH2C12 layer was separated. The CH2C12 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by reverse phase (ODS) column chromatography (10% CH2C12-MeOH:wa- ter=8:2 to 9:1) and the fractions containing the product were dried under reduced pressure to obtain the title compound (90 mg) as a reddish black powdet10355] ?H-NMR 400 MHz (CDC13): oe 6.69-6.18 (14H, m),5.58 (2H, dd), 3.62-3.47 (8H, m), 2.15-2.03 (4H, m), 2.00 (6H, s), 1.99 (6H, s), 1.92 (6H, s), 1.36 (6H, s), 1.24 (6H, s) 10356] Mass spectrum: -ESI, mlz=859.54 (M-H-) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; | Compound 2 (121 mg, 0.25 mmol) was dissolved in methylene chloride (5 ml), DCC (N, N'-dicyclohexylcarbodiimide, 62 mg, 0.3 mmol), HOBT (1-hydroxybenzotriazole , 40 mg, 0.3 mmol), TEA (N, N-diethylethanamine, 52 uL, 0.375 mmol),Thiodiglycolic acid (19 mg, 0.125 mmol) was then added and after the reaction was complete, the solvent was removed under reduced pressure and extracted to give a reddish solid (105 mg, 80%) after column separation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 25h; | CUR (80.0 mg, 0.22 mmol) was dissolved in CH2Cl2, and then Slinker (15.0 mg, 0.1 mmol), EDC·HCl (76.8 mg, 0.40 mmol), and DMAP(2.5 mg, 0.02 mmol) were added continuously. The reaction kept for 1 hwith stir at ambient temperature in closed and shading environment.After that, extra EDC·HCl (39.4 mg, 0.20 mmol) and DMAP (2.5 mg,0.21 mmol) were added, and reaction was stirred for else 24 h withsame condition. After reaction, the organic solvent was evaporatedthrough rotary evaporator. The solid product was dissolved in 5 mL ofDMSO, then 15 mL of distilled water was added. The above dispersionwas dialyzed against distilled water for 24 h using dialysis membrane(1 kD MWCO, 45mm Flat width, Solarbio, USA). Finally, the dialyzeddispersion was lyophilized at -80 C for 24 h, and the final product(CUR-S-CUR) was stored at -20 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 80℃; for 8h; | To a 2L four-necked flask, 150 g (1.0 mol) of L-methionine, 166.8 g (1.2 mol) of bromoacetic acid, and 800 ml of water were added, and the mixture was stirred uniformly, and slowly heated to 80 C for 8 hours. Recovering solvent water under reduced pressure and reduced pressure. A total of 303.4 g of a mixture of L-homoserine lactone hydrobromide, (methylthio)acetic acid and thiodiacetic acid was obtained, and the next step reaction was carried out without isolation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 80℃; for 8h; | To a 2L four-necked flask, 150 g (1.0 mol) of D-methionine, 141.8 g (1.5 mol) of chloroacetic acid, and 1 L of water were added, and the mixture was stirred uniformly, and slowly heated to 80 C for 8 hours. Recovering solvent water under reduced pressure and reduced pressure. A total of 268.4 g of a mixture of D-homoserine lactone hydrochloride, (methylthio)acetic acid and thiodiacetic acid was obtained, and the next step reaction was carried out without isolation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 80.0℃; for 8h; | 540 g (3.6 mol) of DL-methionine, 408 g (4.32 mol) of chloroacetic acid, and 3 L of water were added to a 5 L four-necked flask, and the mixture was stirred uniformly, and slowly heated to 80 C for 8 hours. After the reaction was completed, recovering solvent water under reduced pressure and reduced pressure, respectively, obtained 936 g of a mixture of DL-homoserine lactone hydrochloride, (methylthio)acetic acid, and thiodiacetic acid, and directly proceeded to the next step without isolation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With polyphosphoric acid; at 180℃; | General procedure: 4-Fluoro-2-aminophenol (1, 5 mmol) and 2.5 mmol of thecorresponding carboxylic acid derivatives 2-5 dissolved in10 cm3 PPA are heated under reflux in a flask equipped witha reflux condenser and a magnetic stirrer in an oil bath at180 C for a period of 13-15 h. The reaction was followedby thin layer chromatography (TLC). UV (ultraviolet) lightwas used in the determination of stains in the works of TLC(Kieselgel 60 F254, ready-to-use aluminum plate coatedwith 0.2 mm thickness) which was made using ready-madeplates. After cooling, the reaction mixture was poured ontoice water and neutralized by mixing with 5 N NaOH untilslightly basic (pH 8-9) to get the precipitate. The resultingprecipitate was filtered off and washed with cold water. Lateron, these precipitates were crystallized with a suitable solvent.The resulting crystalline compounds were filtered andthe vacuumed product was dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: thiodiacetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: oleoyl alcohol In dichloromethane Stage #3: curcumin Further stages; | 1 Synthesis of curcumin-oleyl alcohol prodrug (Cur-S-OA) linked by monosulfide bond Weigh a certain amount of thiodiacetic acid and dissolve it in dichloromethane, then add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), p-dimethylaminopyridine (DMAP) After stirring and reacting at room temperature for 0.5h, a certain amount of oleyl alcohol is added to continue stirring for 2-5h, the degree of reaction progress is monitored by TLC, and column chromatography is separated to obtain the carboxylated product of oleyl alcohol substituted by one-sided carboxyl group. Then the resulting oleyl alcohol carboxylation product, EDCI, DMAP, 1-hydroxybenzotriazole (HOBT), and N,N-diisopropylethylamine (DIPEA) were stirred and reacted at room temperature for 0.5h,Curcumin was added, and the reaction was continued to be stirred for 24 h at room temperature under N2 protection, and finally the product was separated and purified by column chromatography. The structure of the prodrug in Example 1 was determined by 1H-NMR. The solvent was selected as CDCl3. The results are shown in Figure 1. The analytical results are as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.25% | In methanol at 20℃; | i. (4-methylbenzo[d]thiazol-2-amine): (thiodiglycolic acid) [(HL + ) . (Htdgca -)] (9) To a methanol solution (8 ml) of 4-methylbenzo[d]thiazol-2- amine (32.8 mg, 0.2 mmol) was added thiodiglycolic acid (30.0 mg, 0.2 mmol). The solution was left standing at room temperature for several days, colorless crystals were isolated after slow evapora- tion of the methanol solution in air. The crystals were dried in air to give [(HL + ) . (Htdgca -)] (9) . Yield: 44.8 mg, 71.25%. m. p. 139-141 °C. Anal. Calcd for C 12 H 14 N 2 O 4 S 2 (314.37): C, 45.80; H, 4.45; N, 8.91; S, 20.36. Found: C, 45.71; H, 4.32; N, 8.80; S, 20.25. In- frared spectrum (KBr disk, cm -1 ): 3728s( ν(OH)), 3467s( νas (NH)), 3345s( νs (NH)), 3271 m, 3146 m, 3070 m, 2959 m, 2933 m, 2871 m, 2854 m, 1669s( ν(C = O)), 1620 m, 1592s( νas (CO 2 -)), 1550 m, 1507 m, 1467 m, 1424 m, 1382s( νs (CO 2 -)), 1341 m, 1296s( ν(C-O)), 1253 m, 1211 m, 1168 m, 1125 m, 1081 m, 1038 m, 994 m, 955 m, 913 m, 868 m, 824 m, 780 m, 739 m, 696 m, 655 m, 615 m, 604 m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.4 g | With acetic anhydride; triethylamine In water monomer; acetone at 175℃; for 0.0416667h; Flow reactor; | 4 Preparation of erdosteine with formation in situ of internal anhydride A solution of thiodi glycolic acid (100 g) in acetone (400 mL), a solution of acetic anhydride (68.3 g) in acetone (370 mL), and a solution of homocysteine thiolactone hydrochloride (96 g) in water (160 mL), acetone (540 mL) and triethylamine (63.2 g), are prepared. The first two solutions are pumped into the first module of a microreactor with an internal volume of 2.7 mL at flow rates of 0.65 mL/min at 175°C. The output of the first module is pumped simultaneously with the third solution into the second module of the microreactor with an internal volume of 2.7 mL at flow rates of 1.2 mL/min (total residence time 2.5 minutes) at 175°C. 450 mL is collected, the acetone is evaporated, and the residue is diluted with isopropanol. After filtration and drying, 24.4 g of pure erdosteine is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: thiodiacetic acid With trifluoroacetic anhydride In ethyl acetate at 20℃; for 24h; Stage #2: methanol With triethylamine In dichloromethane; ethyl acetate at 20℃; for 24h; | 2-((2-Methoxy-2-oxoethyl)thio)acetic acid (11e) To a solution of 2,2'-thiodiacetic acid (500 mg, 3.33 mmol) in ethyl acetate (27 mL) in a roundbottomflask trifluoroacetic anhydride (1.8 g, 8.33 mmol) was added in one portion. The reactionmixture was left stirring at room temperature for one day and then concentrated under reducedpressure. The resulting crude anhydride was mixed with dry DCM (3 mL) and then addedS4dropwise to a stirred mixture of triethylamine (674 mg, 6.66 mmol) and methanol (25 mL) atroom temperature. After 1 day the mixture was concentrated under reduced pressure, followedby addition of DCM (20 mL) and water (20 mL). The pH of aqueous layer was adjusted to 1with concentrated HCl under cooling with ice. The aqueous layer was extracted with DCM(3×20 mL), then combined organic phase was washed with water, dried over Na2SO4 andevaporated to give pure title compound. Yield 25% (62 mg). 1H NMR (400 MHz, CDCl3) δ9.64 (s, 1H), 3.74 (s, 3H), 3.43 (s, 2H), 3.41 (s, 2H). 13C NMR (101 MHz, CDCl3) δ 175.5,170.5, 52.7, 46.0, 33.68, 33.63. HRMS (ESI) m/z: [M+Na]+ alcd for C5H8SNaO4+ 187.0036;Found 187.0039 |
Tags: 123-93-3 synthesis path| 123-93-3 SDS| 123-93-3 COA| 123-93-3 purity| 123-93-3 application| 123-93-3 NMR| 123-93-3 COA| 123-93-3 structure
[ 2068-24-8 ]
2,2'-(Methylenebis(sulfanediyl))diacetic acid
Similarity: 0.83
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :