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) ]} | {[ 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. : | 13750-63-5 | MDL No. : | MFCD08236826 |
Formula : | C5H7NOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CQMPPPAHJBQCOY-UHFFFAOYSA-N |
M.W : | 129.18 g/mol | Pubchem ID : | 17750909 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 33.21 |
TPSA : | 61.36 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) : | -6.73 cm/s |
Log Po/w (iLOGP) : | 1.46 |
Log Po/w (XLOGP3) : | 0.5 |
Log Po/w (WLOGP) : | 0.79 |
Log Po/w (MLOGP) : | -0.47 |
Log Po/w (SILICOS-IT) : | 2.35 |
Consensus Log Po/w : | 0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.35 |
Solubility : | 5.74 mg/ml ; 0.0444 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.36 |
Solubility : | 5.66 mg/ml ; 0.0438 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.47 |
Solubility : | 4.35 mg/ml ; 0.0337 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.17 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | 1760 |
Hazard Statements: | H318 | Packing Group: | Ⅲ |
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 |
---|---|---|
60% | Method B: Alternatively, dissolve 4-methyl-thiazole-2-carboxylic acid ethyl ester (prepare in 27% yield according to the procedures essentially as described in Erlenmeyer, H., et al., HeIv. CHm. Acta (1944), 27, 1437-1438) (1.52 g, 8.88 mmol) in THF (6OmL) and add lithium borohydride (2.0M solution in THF, 9 mL, 17.8 EPO <DP n="136"/>mmol). Heat at reflux temperature for 18 h. Allow to cool to room temperature and dilute the reaction mixture with water (20 mL). Extract into ethyl acetate (3 x 50 mL). Dry the combined organic portions (MgSO4), filter, and concentrate in vacuo at 45 0C. Purify the crude product on silica gel (40 g) with 40 - 80% EtOAc/hexanes to give 690 mg (60%) of the title compound as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | at 0 - 20℃; for 18h; | Preparation 37; 2-Bromomethyl-5-chloro-thiopheneCool (5-chloro-thiophen-2-yl)-methanol (Preparation 30) (330 mg, 2.22 mmol) to 0 0C and add acetyl bromide (709 mg, 430 muL, 5.76 mmol). Allow to warm to room temperature over 18 h, dilute with EtOAc (10 mL), and cautiously add saturated aqueous NaHCO3 (3 mL). When the carbon dioxide evolution stops, load the mixture onto a Varian Chem Elut CE1005 solid phase extraction cartridge (Varian part number 12198006). Elute with EtOAc, collect, and concentrate about 50 mL to obtain the crude product. Purify on silica gel (12 g) using 0-15% EtOAc/hexanes to afford 250 mg (53%) of the title compound as a yellow oil. MS (EI): 210,212; 1H NMR (CDCl3): delta 6.92 (d, IH, /=3.5 Hz), 6.78 (d, IH, /=4.0 Hz), 4.66 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1: Preparation of Selected Beta-Secretase Inhibitor Compounds; Example 1.1: Synthesis of tert-butyl 3-hydroxy-4-(3-methoxybenzylammo)-l- phenylbutan-2-ylcarbamate; [0215] Methylthiazole (1.0 g, 10.1 mmol) in THF at - 78 0C was treated with n-BuLi (1.6 M, 7.56 niL) for 30 min, DMF (1.4 mL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material was disappeared (by TLC), the reaction mixture was recooled to 0 0C and LAH (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqueous NH4Cl, diluted with EtOAc. The organic solution was separated, extracted twice with EtOAc, dried with Na2SO4, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDCl3), delta: 6.89 (s, 1 H); 4.95 (s, 2 H); 2.48 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | Preparation 34; Methanesulfonic acid 4-methyl-thiazol-2-ylmethyl esterCombine 4-methyl-thiazol-2-yl)-methanol (Preparation 30) (1.00 g, 7.74 mmol) and triethylamine (1.25 g, 1.73 mL, 12.4 mmol) in dichloromethane (30 mL) with stirring and cool to 0 0C under nitrogen. Add methanesulfonyl chloride (931 mg, 633 muL, 8.13 mmol) to the reaction mixture and stir at 0 0C for 30 min. Warm to room temperature over 30 min, then dilute with water (40 mL) and dichloromethane (40 mL). Separate the layers, dry the organic portion (MgSO4), filter, and concentrate in vacuo at 40 0C to afford 1.15 g (72%) of the title compound as a brown oil. MS (ES): m/z 208 (M+l); 1H NMR (CDCl3): delta 7.03 (m, IH), 5.48 (s, 2H), 3.11 (s, 3H), 2.50 (d, 3H, 7=0.9 Hz). |
With triethylamine; In dichloromethane; at 0℃; for 0.333333h; | Methylthiazole methanol (0.57 g, 4.4 mmol) was treated with mesyl chloride (0.42 mL, 5.4 mmol) and triethyl ethylamine at 0 0C in dichloromethane . The resulting mixture was stirred for 20 minutes followed by quenching with aqueous NH4Cl. Evaporation of the solvent from the organic layer and flash chromatography of the residue afforded the corresponding mesylate as an oil. The mesylate (0.25g, 1.2 mmol) was then dissolved in DMF and sodium azide (0.62g, 9.6 mmol) was added. The mixture was heated to reflux for 2 hours followed by cooling and washing with aqueous NH4Cl. Evaporation of the solvent from the organic layer resulted in the corresponding azide. The azide (0.14g, 0.91 mmol) was EPO <DP n="52"/>dissolved in ethyl acetate, Pd(OH)2 (0.07g) was added, and the suspension was stirred under a hydrogen atmosphere for 5 hours. The suspension was filtered through Celite. Evaporation of the solvent and flash chromatography of the residue afforded methylthiazole methylamine as a yellow oil. 1H-NMR: (300 MHz, CDCl3), delta: 6.74 (m, 1 H); 4.09 (m, 2 H); 2.37 (s, 3 H). | |
With triethylamine; In dichloromethane; at 0℃; for 0.333333h; | Methylthiazole methanol (0.57 g, 4.4 mmol) was treated with mesyl chloride (0.42 mL, 5.4 mmol) and triethyl ethylamine at 0 0C in dichloromethane. The resulting mixture was stirred for 20 minutes followed by quenching with aqueous NH4Cl. Evaporation of the solvent from the organic layer and flash chromatography of the residue afforded the corresponding mesylate as an oil. The mesylate (0.25g, 1.2 mmol) was then dissolved in DMF and sodium azide (0.62g, 9.6 mmol) was added. The mixture was heated to reflux for 2 hours followed by cooling and washing with aqueous NH4Cl. Evaporation of the solvent from the organic layer resulted in the corresponding azide. The azide (0.14g, 0.91mmol) was dissolved in ethyl acetate, Pd(OH)2 (0.07g) was added, and the suspension was stirred under a hydrogen atmosphere for 5 hours. The suspension was filtered through Celite. Evaporation of the solvent and flash chromatography of the residue afforded methylthiazole methylamine as a yellow oil. 1H-NMR: (300 MHz, CDCl3), d: 6.74 (m, 1 H); 4.09 (m, 2 H); 2.37 (s, 3 H). |
With triethylamine; In dichloromethane; at 0℃; for 0.333333h; | Methylthiazole methanol (0.57 g, 4.4 mmol) was treated with mesyl chloride (0.42 mL, 5.4 mmol) and triethyl ethylamine at 0 0C in dichloromethane. The resulting mixture was stirred for 20 minutes followed by quenching with aqueous NH4Cl. Evaporation of the solvent from the organic layer and flash chromatography of the residue afforded the corresponding mesylate as an oil. The mesylate (0.25g, 1.2 mmol) was then dissolved in DMF and sodium azide (0.62g, 9.6 mmol) was added. The mixture was heated to reflux for 2 hours followed by cooling and washing with aqueous NH4Cl. Evaporation of the solvent from the organic layer resulted in the corresponding azide. The azide (0.14g, 0.91mmol) was dissolved in ethyl acetate, Pd(OH)2 (0.07g) was added, and the suspension was stirred under a hydrogen atmosphere for 5 hours. The suspension was filtered through Celite. Evaporation of the solvent and flash chromatography of the residue afforded the desired methylthiazole methylamine as a yellow oil. 1H-NMR: (300 MHz, CDCl3), d: 6.74 (m, 1 H); 4.09 (m, 2 H); 2.37 (s, 3 H). | |
With triethylamine; In dichloromethane; at 0℃; for 0.333333h; | [0270] Methylthiazole methanol (0.57 g, 4.4 mmol) was treated with mesyl chloride (0.42 mL, 5.4 mmol) and triethyl ethylamine at 0 C in dichloromethane. The resulting mixture was stirred for 20 minutes followed by quenching with aqueous NH4C1. Evaporation of the solvent from the organic layer and flash chromatography of the residue afforded the corresponding mesylate as an oil. The mesylate (0.25g, 1.2 mmol) was then dissolved in DMF and sodium azide (0.62g, 9.6 mmol) was added. The mixture was heated to reflux for 2 hours followed by cooling and washing with aqueous NH4C1. Evaporation of the solvent from the organic layer resulted in the corresponding azide. The azide (0.14g, 0.91mmol) was dissolved in ethyl acetate, Pd(OH)2 (0.07g) was added, and the suspension was stirred under a hydrogen atmosphere for 5 hours. The suspension was filtered through Celite. Evaporation of the solvent and flash chromatography of the residue afforded the desired methylthiazole methylamine as a yellow oil. 1H-NMR: (300 MHz, CDC13), delta: 6.74 (m, 1 H); 4.09 (m, 2 H); 2.37 (s, 3 H). | |
With triethylamine; In dichloromethane; at 0℃; for 0.333333h; | Methylthiazole methanol (0.57 g, 4.4 mmol) was treated with mesyl chloride (0.42 mL, 5.4 mmol) and triethyl ethylamine at 0 C in dichloromethane. The resulting mixture was stirred for 20 minutes followed by quenching with aqueous NH4C1. Evaporation of the solvent from the organic layer and flash chromatography of the residue afforded the corresponding mesylate as an oil. The mesylate (0.25g, 1.2 mmol) was then dissolved in DMF and sodium azide (0.62g, 9.6 mmol) was added. The mixture was heated to reflux for 2 hours followed by cooling and washing with aqueous NH4C1. Evaporation of the solvent from the organic layer resulted in the corresponding azide. The azide (0.14g, 0.91mmol) was dissolved in ethyl acetate, Pd(OH)2 (0.07g) was added, and the suspension was stirred under a hydrogen atmosphere for 5 hours. The suspension was filtered through Celite. Evaporation of the solvent and flash chromatography of the residue afforded the desired methylthiazole methylamine as a yellow oil. 1H-NMR: (300 MHz, CDC13), delta: 6.74 (m, 1 H); 4.09 (m, 2 H); 2.37 (s, 3 H). | |
With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | III. Methanesulfonic acid 4-methyl-thiazol-2-ylmethyl ester To a stirred solution of <strong>[13750-63-5](4-methyl-thiazol-2-yl)-methanol</strong> (1.5 g, 11.6 mmol) and Et3N (4.85 mL, 34.8 mmol) in DCM (50 mL) was added MsCl (2.7 mL, 34.8 mmol) in dropwise at 0C. After the additional, the mixture was stirred for 1 hour at room temperature. The reaction mixture was quenched by water (15 mL), extracted with ethyl acetate (3 x 20 mL). The combined organic phase was dried over Na2S04, filtered and concentrated in vacuum to give the crude product methanesulfonic acid 4-methyl-thiazol-2- ylmethyl ester (2.4 g, 100% yield): lR NMR (400 MHz, CDC13) delta 7.01 (s, 1H), 5.43 (s, 2H), 3.13 (s, 3H), 2.46 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; | EXAMPLE 39 When 2-chloromethyl-4-methyltriazole [prepared by the reaction of thionyl chloride and 2-hydroxymethyl-4-methylthiazole, which itself is prepared according to the procedure of J. Chem. Soc., (Suppl. Issue No. 1), S106-111 (1966) or Acta Chem. Scand., 20, 2649 (1966)] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide, and the resultant amine is treated with 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide, there is produced 3-methoxy-4-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}-1,2,5-thiadiazole 1,1-dioxide. | |
With thionyl chloride; | EXAMPLE 39 When 2-chloromethyl-4-methylthiazole [prepared by the reaction of thionyl chloride and 2-hydroxymethyl-4-methylthiazole, which itself is prepared according to the procedure of J. Chem. Soc., (Suppl. Issue No. 1), S106-111 (1966) or Acta Chem. Scand., 20, 2649 (1966)] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide, and the resultant amine is treated with 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide, there is produced 3-methoxy-4-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}-1,2,5-thiadiazole 1,1-dioxide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; | EXAMPLE 15 When 2-chloromethyl-4-methylthiazole [prepared by the reaction of thionyl chloride and 2-hydroxymethyl-4-methylthiazole, which itself is prepared according to the procedure of J. Chem. Soc., (Suppl. Issue No. 1), S106-111 (1966) or Acta Chem. Scand., 20, 2649 (1966)] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide, and the resultant amine is treated with 1,1-bis(methylthio)-2-nitroethylene, there is produced 1-nitro-2-methylthio-2-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}ethylene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; | EXAMPLE 16 When 2-chloromethyl-4-methylthiazole [prepared from 2-hydroxymethyl-4-methylthiazole and thionyl chloride] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide and the resultant amine treated with dimethyl cyanodithioimidocarbonate there is produced N-cyano-N'-{2-[(4-methylthiazol-2-yl)methylthio]ethyl}-S-methylisothiourea. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
461.0 mg (87%) | In dichloromethane; dimethyl sulfoxide; | EXAMPLE 22D 4-methylthiazole-5-carboxaldehyde A 3-neck, 100 mL round-bottom flask was charged with anhydrous CH2Cl2 (15 mL) and oxalyl chloride (0.54 mL, 6.24 mmol) under N2 atmosphere. The mixture was cooled to -78 C. Anhydrous DMSO (0.59 mL, 8.32 mmol) was slowly added. The reaction was allowed to stir for 30 minutes. The product from Example 22C (537.5 mg, 4.16 mmol) in CH2Cl2 (5 mL) was slowly added. The reaction was allowed to stir for approximately 3 hours, until TLC (1:1 EtOAc/hexanes) showed no starting material. The reaction was quenched with triethylamine (2.4 mL, 16.64 mmol) and stirred for 10 minutes before warming to room temperature. The reaction was poured into Et2O (100 mL) and extracted with water (2*25 mL). The organic phase was washed with NaHCO3 (25 mL) and brine. The organic phase was dried (MgSO4) and concentrated under vacuum. The crude product was stored in the freezer to provide 461.0 mg (87%) of the title compound as an orange crystalline solid. 1H NMR (300 MHz, CDCl3) delta 10.15, s, 1H; 8.9, s, 1H; 2.8, s, 3H. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1Synthesis of Heterocycle AlcoholsExample 1.1; Methylthiazole Methanol Methylthiazole (1.0 g, 10.1 mmol) in THF at -78 C. was treated with n-BuLi (1.6 M, 7.56 mL) for 30 min, DMF (1.4 mL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material was disappeared (by TLC), the reaction mixture was recooled to 0 C. and LAH (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqeuous NH4Cl, diluted with EtOAc. The organic solution was separated, extracted twice with EtOAc, dried with Na2SO4, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDCl3), delta: 6.89 (s, 1H); 4.95 (s, 2H); 2.48 (s, 3H). | ||
Example 1.1: Synthesis of Amine Building Blocks.; Example 1.1.1: (4-methylthiazol-2-yl)methanamine; Methylthiazole (1.0 g, 10.1 mmol) in THF at - 78 0C was treated with n-BuLi (1.6 M, 7.56 mL) for 30 min, DMF (1.4 rnL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material disappeared (by TLC), the reaction mixture was recooled to 0 0C and LAH (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqueous NH4Cl, diluted with EtOAc. The organic solution was separated, extracted twice with EtOAc, dried with Na2SO4, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDCl3), d: 6.89 (s, 1 H); 4.95 (s, 2 H); 2.48 (s, 3 H). | ||
[0269] Methylthiazole (1.0 g, 10.1 mmol) in THF at - 78 C was treated with n-BuLi (1.6 M, 7.56 mL) for 30 min, DMF (1.4 mL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material disappeared (by TLC), the reaction mixture was recooled to 0 C and LAH (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqueous NH4C1, diluted with EtOAc. The organic solution was separated, extracted twice with EtOAc, dried with Na2S04, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDC13), delta: 6.89 (s, 1 H); 4.95 (s, 2 H); 2.48 (s, 3 H). |
Methylthiazole (1.0 g, 10.1 mmol) in tetrahydrofuran (THF) at - 78 C was treated with n-BuLi (1.6 M, 7.56 mL) for 30 min, dimethylformamide (DMF) (1.4 mL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material disappeared (by TLC), the reaction mixture was recooled to 0 C and lithium aluminum hydride (LAH) (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqueous NH4C1, diluted with ethyl acetate (EtOAc). The organic solution was separated, extracted twice with EtOAc, dried with Na2S04, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDC13), delta: 6.89 (s, 1 H); 4.95 (s, 2 H); 2.48 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; In acetonitrile; at 20℃; for 15h; | Example 2.8Synthesis of Heterocycle Mixed Carbonate; To a stirred solution of 4-methyl thiazole methanol (0.47 g, 3.6 mmol) in CH3CN (15 mL) was added triethylamine (1.5 mL, 11 mmol) and N,N'-disuccinnimidyl carbonate (1.12 g, 4.4 mmol). The resulting mixture was stirred at room temperature for 15 h and was concentrated under reduced pressure. The residue was dissolved in EtOAc and saturated NaHCO3. The layers were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide mixed carbonate 8e (955 mg, 97%) which was used for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1.1: Synthesis of Amine Building Blocks.; Example 1.1.1: (4-methylthiazol-2-yl)methanamine; Methylthiazole (1.0 g, 10.1 mmol) in THF at - 78 0C was treated with n-BuLi (1.6 M, 7.56 mL) for 30 min, DMF (1.4 rnL, 18.2 mmol) was added dropwise. The resulting reaction mixture was warmed to r.t. After the starting material disappeared (by TLC), the reaction mixture was recooled to 0 0C and LAH (0.69 g, 18.5 mmol) was added. The mixture was warmed to r.t. and stirred for 1 h, the reaction was quenched with aqueous NH4Cl, diluted with EtOAc. The organic solution was separated, extracted twice with EtOAc, dried with Na2SO4, and concentrated. The residue was purified with flash chromatography to give the corresponding alcohol as a light yellow oil. 1H-NMR: (300 MHz, CDCl3), d: 6.89 (s, 1 H); 4.95 (s, 2 H); 2.48 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;Product distribution / selectivity; | Diphenylphosphoryl azide (DPPA) (1.2 eq) and l,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) (1.2 eq) were added to a stirred solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (1 eq) in 7 ml anh. toluene under Ar. After stirring overnight, the solvent was removed in vacuo. Purification via flash chromatography yielded2-(azidomethyl)-4-methylthiazole. | |
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;Inert atmosphere; | 0272] Diphenylphosphoryl azide (DPPA) (1.2 eq) and l,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) (1.2 eq) were added to a stirred solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (1 eq) in 7 ml anh. toluene under Ar. After stirring overnight, the solvent was removed in vacuo.Purification via flash chromatography yielded2-(azidomethyl)-4-methylthiazole. | |
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene;Inert atmosphere; | Diphenylphosphoryl azide (DPPA) (1.2 eq) and l,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) (1.2 eq) were added to a stirred solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (1 eq) in 7 ml anh. toluene under Ar. After stirring overnight, the solvent was removed in vacuo.Purification via flash chromatography yielded2-(azidomethyl)-4-methylthiazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 50℃; | PREPARATION 115(5-Bromo-4-methyl-thiazol-2-yl)-methanolTo a solution of 4-methyl-thiazole (10 g, 100 mmol) in dry THF (300 mL) was added n- BuLi in hexane (60 mL, 150 mmol, 2.5 M) dropwise at -70C, and the mixture was stirred at -70C for 1.5 hour, DMF (12 mL) was added to the slurry over 15 min, and the mixture was stirred at -70C for 3 hours. TLC (petroleum etherEtOAc 10:1 ) indicated the reaction was completed. The mixture was warmed to 0C, and poured onto wet-ice. The mixture was acidified by 2N HCI to pH ~ 4, and extracted with EtOAc (100 mL chi 3). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate, and concentrated in vacuum to give 4-methyl-thiazole-2-carbaldhyde (10 g, 78.7%) as brown oil.To a solution of 4-methyl-thiazole-2-carbaldhyde (10.0 g, 78 mmol) in dry THF (80 mL) was added NaBH4 (1.49 g, 39 mmol), and the mixture was stirred at room temperature for 2 hours. TLC (petroleum etherEtOAc 2:1 ) indicated the reaction was completed. The mixture was diluted with NH4CI solution (50 mL) and the mixture was filtered. The filtrate was extracted with EtOAc (50 mL chi 3). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, and concentrated in vacuum to give the residue which was purified by a silica gel column eluting with petroleum etherEtOAc 3:1 to give (4-Methyl-thiazol-2-yl)-methanol (7 g, 70%) as a yellow oil.To a solution of <strong>[13750-63-5](4-methyl-thiazol-2-yl)-methanol</strong> (7.0 g, 54.3 mmol) in DMF (80 mL) was added NBS (10.6 mg, 59.6 mmol), and the mixture was stirred at 50C overnight. TLC (petroleum etherEtOAc 2:1 ) indicated the reaction was completed. The mixture was diluted with H20 (50 mL) and extracted with EtOAc (50 mL chi 3). The combined organic layers were washed with brine (50 mL 3), dried over sodium sulfate, and concentrated in vacuum to give the residue which was purified by a silica gel column (petroleum etherEtOAc 10:1 ) to give the title compound (1 1.2 g, 99%) as a brown solid. |
78% | With N-Bromosuccinimide; In acetonitrile; at 20℃; for 2h; | To a solution of 29 (10.0 g, 77 mmol) in MeCN (387 mL) was added NBS (13.8 g, 77.0 mmol) at room temperature. After being stirred for 2 h at room temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with saturated aqueous NH4Cl solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 33% EtOAc in hexane) to give 12.6 g (78%) of 30 as yellow solid. 1H NMR (400 MHz, CDCl3)d 2.37 (3H, s), 2.74 (1H, brs), 4.85 (2H, s). |
75% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 50℃; for 2h; | To a solution of thiazole 21a (720 mg, 5.58 mmol) in DMF (15 mL) was added NBS (1.1 g, 6.14 mmol) and the mixture was stirred at 50C for 2 hours. After the completion of the reaction, the mixture was diluted with water and was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give a residue which was purified in ISCO max gradient 40% EtOAc/hexane to give the pure product (870 mg, 75% yield). 1H NMR (CDCl3, 400 MHz) 8: 4.83 (s, 2H), 4.01 (bs, 1H), 2.36 (s, 3H). |
With N-Bromosuccinimide; In N,N-dimethyl-formamide;Reflux; | To a solution of Intermediate 53 (252 mg) in DMF was added N-bromosuccinimide (385 mg). The mixture was heated under reflux overnight. The solvent was evaporated under vacuum and the residue obtained was purified by column chromatography on silica gel using hexane/EtOAc as eluent to give 95 mg of the title compound as a brown solid. 1H-NMR (delta, ppm, CDCl3): 4.86 (s, 2H), 2.38 (s, 3H). |
Tags: 13750-63-5 synthesis path| 13750-63-5 SDS| 13750-63-5 COA| 13750-63-5 purity| 13750-63-5 application| 13750-63-5 NMR| 13750-63-5 COA| 13750-63-5 structure
[ 774239-03-1 ]
2-(Hydroxymethyl)thiazole-4-carbaldehyde
Similarity: 0.90
[ 76632-23-0 ]
(2-Methylthiazol-4-yl)methanol
Similarity: 0.90
[ 99839-16-4 ]
(4,5-Dimethylthiazol-2-yl)methanol
Similarity: 0.83
[ 156589-83-2 ]
(4-Isopropylthiazol-2-yl)methanol
Similarity: 0.83
[ 774239-03-1 ]
2-(Hydroxymethyl)thiazole-4-carbaldehyde
Similarity: 0.90
[ 76632-23-0 ]
(2-Methylthiazol-4-yl)methanol
Similarity: 0.90
[ 14542-16-6 ]
4-Methylthiazole-2-carboxylic 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 :