[ CAS No. 37143-54-7 ] {[proInfo.proName]}

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Quality Control of [ 37143-54-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 37143-54-7 ]

Product Details of [ 37143-54-7 ]

CAS No. :	37143-54-7	MDL No. :	MFCD00008084
Formula :	C₄H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	89.14	Pubchem ID :	-
Synonyms :

Safety of [ 37143-54-7 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P210-P273-P280-P305+P351+P338-P310	UN#:	2733
Hazard Statements:	H225-H302-H314-H412	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 37143-54-7 ]

* 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.

Downstream synthetic route of [ 37143-54-7 ]

[ 37143-54-7 ] Synthesis Path-Downstream 1~26

1
[ 10500-24-0 ]
[ 37143-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; chloroform; sulfuric acid

Reference： [1]Sutton; Data [Journal of the American Pharmaceutical Association (1912), 1952, vol. 41, p. 328,331]

2
[ 1143-72-2 ]
[ 37143-54-7 ]
[ 87119-03-7 ]
{2,4-dihydroxy-3-[(1-methoxyprop-2-yl)amino]phenyl}phenylmethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 37% 2: 23%	With lithium perchlorate In methanol at 25℃; Electrolysis;

Reference： [1]Largeron, Martine; Neudorffer, Anne; Fleury, Maurice-Bernard [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 12, p. 2721 - 2727]

3
[ 37143-54-7 ]
[ 66131-68-8 ]
<i>N</i>²-(2-methoxy-1-methyl-ethyl)-<i>N</i>⁴-methyl-pyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3510 - 3513

4
[ 175357-98-9 ]
[ 37143-54-7 ]
C₁₁H₁₃FN₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;

Reference： [1]Harbottle, Gareth W.; Feeder, Neil; Gibson, Karl R.; Glossop, Mel; Maw, Graham N.; Million, William A.; Morel, Florence F.; Osborne, Simon; Poinsard, Cedric [Tetrahedron Letters, 2007, vol. 48, # 24, p. 4293 - 4296]

5
[ 15897-81-1 ]
[ 37143-54-7 ]
N-2-(1-methoxypropyl)-1-adamantanecarboxamide [ No CAS ]

Reference： [1]Patent: US6348625,2002,B1 .Location in patent: Page column 4

6
[ 79-04-9 ]
[ 37143-54-7 ]
[ 127727-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 1h;	21 EXAMPLE 21; N-(2-Methoxy-1-methyl-ethyl)-2-piperazin-1-yl-acetamide; 2-Methoxy-1-methyl-ethylamine (15 mmol) and diisopropylethylamine (17 mmol) were diluted with methylene chloride to give a total volume of 8 mL. The amine solution was added in a portion-wise fashion via a syringe to a solution of chloroacetylchloride (13 mmol) in methylene chloride (10 mL) cooled to approximately 40° C. in a sealed 40 mL vial. The reaction mixture was stirred for 1 h at reduced temperature. The solution was then made acidic with 1N hydrochloric acid and then diluted with 10 mL of methylene chloride. The vial was agitated and centrifuged. The organic layer was transferred to 40 mL vials and concentrated in vacuo. The residue (1.69 g, 10.21 mmol) was diluted with 10 mL of dimethylformamide. Piperazine-1-carboxylic acid tert-butyl ester (8.67 mmol) and diisopropylethylamine (13.27 mmol) were added. The reaction mixture was shaken at 65° C. overnight and concentrated in vacuo. The crude residue was dissolved in 10 mL of dioxane and 10 mL of 4 M hydrochloric acid in dioxane. The solution was shaken overnight at room temperature then centrifuged. The supernatant was removed, and the remaining solids were shaken with hexanes then centrifuged. The supernatant was removed, and the solids was collected and dried in vacuo to give N-(2-methoxy-1-methylethyl)-2-piperazin-1-yl-acetamide. LR-MS: 216.4 [(M+H)+].
	With N-ethyl-N,N-diisopropylamine In dichloromethane at -40℃; for 1h;	15 Methoxy-1-methyl-ethylamine (15 mmol, 1.15 eq) and diisopropylethylamine (17 mmol, 1.3 eq) were diluted with methylene chloride to give a total volume of 8 mL. The amine solution was added in a portion-wise fashion via a syringe to a solution of chloroacetylchloride (13 mmol) in methylene chloride (10 mL) cooled to approximately-40°C in a sealed 40 mL vial. The reaction mixture was stirred for 1 h at reduced temperature. The solution was then made acidic with IN HCI and then diluted with 10 mL of methylene chloride. The vial was agitated and centrifuged. The organic layer was transferred to 40 mL vials and concentrated in vacuo. The residue (1.69 g, 10.21 mmol) was diluted with 10mL of dimethylformamide. Piperazine-1- carboxylic acid tert-butyl ester (8.67 mmol, 0.85 eq) and diisopropylethylamine (13.27 mmol, 1.3 eq) were added. The reaction mixture was shaken at 65 °C overnight and concentrated in vacuo. The crude residue was dissolved in 10 mL of dioxane and 10 mL of 4M hydrochloric acid in dioxane. The solution was shaken overnight at room temperature then centrifuged. The supernatant was removed, and the remaining solids were shaken with hexane then centrifuged. The supernatant was removed, and the solids was collected and dried in vacuo to give N-(2- methoxy-1-methylethyl) -2-piperazin-1-yl-acetamide dihydrochloride. LR-MS: 216.4 [(M+H)+]

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2006/211693, 2006, A1 Location in patent: Page/Page column 24
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2005/110996, 2005, A1 Location in patent: Page/Page column 39

7
[ 58749-33-0 ]
[ 37143-54-7 ]
[ 927672-48-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With caesium carbonate In toluene for 24h; Heating / reflux;	5.46.3 5.46.3 3-(2-Methoxy-1-Methylethylamino)Phthalic Acid Dimethyl Ester To a stirred solution of 3-Bromophthalic acid dimethyl ester (0.82 g, 3.0 mmol) in toluene (20 mL), were added S-BINAP (56 mg, 0.09 mmol), Pd2(dba)3 (55 mg, 0.06 mmol), Cs2CO3 (1.37 g, 4.2 mmol), and 1-methoxy-2-propanamine (0.32 g, 3.6 mmol), and the resulting mixture was heated to reflux with stirring under nitrogen for 24 hours. The mixture was allowed to cool to room temperature, and diethyl ether was added (70 mL). The mixture was filtered, and the filtrate was evaporated in vacuo. The residue was chromatographed eluting with 17:3 hexanes-ethyl acetate. The resulting material was further purified by preparative HPLC, eluting with 11:9 water-acetonitrile, and providing 0.32 g of the product in 38% yield: 1H NMR (DMSO-d6) δ1.14 (d, J=6.4 Hz, 3H), 3.29 (s, 3H), 3.37 (d, J=4.8 Hz, 2H), 3.74 (s, 3H), 3.77 (s, 3H), 3.74-3.80 (m, 1H), 6.53 (d, J=7.8 Hz, 1H), 6.76 (d, J=7.3 Hz, 1H), 6.99 (d, J=8.6 Hz, 1H), 7.38 (t, J=7.8 Hz, 1H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US2007/49618, 2007, A1 Location in patent: Page/Page column 70-71

8
[ 37143-54-7 ]
[ 500353-15-1 ]
[ 942471-16-1 ]

Yield	Reaction Conditions	Operation in experiment
84%		A mixture of <strong>[500353-15-1]2,4-difluoro-benzoic acid tert-butyl ester</strong> (30 g, 140.05 mmol) and (S)-2- methoxy-1-methyl-ethylamine (100 mL) was stirred at 65C for 2 days. A satured solution of NaHCOs was added and the mixture was extracted with dichloromethane (3x). The organic phase was washed with water (2x), brine, dried over sodium sulfate <n="214"/>filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane-EtOAc 9:1). The title compound (33.38 g, 84%) was obtained as oil.IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 7.87 (d, J=7.80 Hz, IH), 7.80 (t, J=7.19 Hz, IH), 6.60 (dd, Jl=13.05 Hz, J2=2.44 Hz, IH), 6.36 (m, IH), 3.80 (m, IH), 3.40 (d, J=4.76 Hz, 2H), 3.30 (s, 3H), 1.53 (s, 9H), 1.17 (d, J=6.58 Hz, 3H).
84%	at 65.0℃; for 48.0h;	A mixture of <strong>[500353-15-1]2,4-difluoro-benzoic acid tert-butyl ester</strong> (30 g, 140.05 mmol) and (S)-2- methoxy-1-methyl-ethylamine (100 mL) was stirred at 65C for 2 days. A satured solution OfNaHCO3 was added and the mixture was extracted with dichloromethane (3 times). The organic phase was washed twice with water then with brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel eluting with exane/ethyl acetate 9:1. The title compound (33.38 g, 84%) was obtained as oil. IH-NMR (400 MHz), delta (ppm, DMSO-J6): 7.87 (d, J=7.80 Hz, IH), 7.80 (t, J=7.19 Hz, IH), 6.60 (dd, Jl=13.05 Hz, J2=2.44 Hz, IH), 6.36 (m, IH), 3.80 (m, IH), 3.40 (d, J=4.76 Hz, 2H), 3.30 (s, 3H), 1.53 (s, 9H), 1.17 (d, J=6.58 Hz, 3H).
84%	at 65.0℃; for 48.0h;	Preparation of 4-fluoro-2-((S)-2-methoxy-l-methyl-ethylamino)-benzoic acid tert- butyl ester; A mixture of <strong>[500353-15-1]2,4-difluoro-benzoic acid tert-butyl ester</strong> (30 g, 140.05 mmol) and (S)-2- methoxy-1-methyl-ethylamine (100 mL) was stirred at 65C for 2 days. A satured solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3 times). The organic phase was washed twice with water then with brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane/ethyl acetate 9:1). The title compound(33.38 g, 84%) was obtained as oil. IH-NMR (400 MHz), delta (ppm, DMSO-J6): 7.87 (d, J=7.80 Hz, IH), 7.80 (t, J=7.19 Hz,IH), 6.60 (dd, Jl=13.05 Hz, J2=2.44 Hz, IH), 6.36 (m, IH), 3.80 (m, IH), 3.40 (d,J=4.76 Hz, 2H), 3.30 (s, 3H), 1.53 (s, 9H), 1.17 (d, J=6.58 Hz, 3H).

Reference： [1]Patent: WO2007/68619,2007,A1 .Location in patent: Page/Page column 212-213
[2]Patent: WO2008/74749,2008,A1 .Location in patent: Page/Page column 74
[3]Patent: WO2009/13126,2009,A1 .Location in patent: Page/Page column 155

9
[ 37143-54-7 ]
[ 261635-93-2 ]
N-(2-methoxy-1-methylethyl)-2-methyl-6-(trifluoromethyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; triethylamine; trifluoroacetic acid In dichloromethane; water; acetonitrile	150 N-(2-methoxy-1-methylethyl)-2-methyl-6-(trifluoromethyl)nicotinamide EXAMPLE 150 N-(2-methoxy-1-methylethyl)-2-methyl-6-(trifluoromethyl)nicotinamide A suspension of 2-methyl-6-(trifluoromethyl)nicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of 2-methoxy-1-methylethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 277 (M+H)+; 1H NMR (DMSO-d6) δ 1.13 (d, 3H), 1.22-1.27 (m, 2H), 2.54 (s, 3H), 2.57 (s, 3H), 3.36-3.40 (m, 1H), 7.78 (d, 1H), 7.92 (d, 1H), 8.46 (d, 1H).

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2004/116479, 2004, A1

10
[ 19646-06-1 ]
[ 37143-54-7 ]
[ 1150111-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In 1-methyl-pyrrolidin-2-one at 200℃; for 0.333333h; Microwave irradiation;	19.A 4,6-Diiodo-pyrimidine is a known compound and was prepared according to Taft,W.E. et al. J. Med. Pharm. Chem., 1962, 5, 1335.A microwave vial was charged with 4,6-diiodopyrimidine (2.0 g, 6.02 mmol), 2-aminomethoxypropane (763 μL, 7.23 mmol), triethylamine (2.1 mL, 15.06 mmol) and N-methylpyrrolidinone (16 mL). The resulting solution was micro waved for 20 min at 200 ºC, then poured into water and extracted with diethyl ether (3 x 30 mL). The organic layers were combined and washed three times with de -ionized water, then dried and concentrated. The residue was subjected to silica gel chromatographic purification using a gradient of hexanes to 40% ethyl acetate in hexanes as eluant to afford 2.O g of the title compound as an oil. 1H NMR (CDCl3) δ 8.2 (s, IH), 6.8 (s, IH), 5.1 (br s, IH), 4.1 (br s, IH), 3.4 (m, 2H), 3.3 (s, 3H), 1.2 (d, 3H).

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2009/61761, 2009, A2 Location in patent: Page/Page column 48

11
[ 37143-54-7 ]
[ 500353-15-1 ]
[ 942471-23-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 65.0℃; for 48.0h;	Preparation of 4-fluoro-2-((R)-2-methoxy-1-methyl-ethylamino)-benzoic acid tert-butyl ester; A mixture of <strong>[500353-15-1]2,4-difluoro-benzoic acid tert-butyl ester</strong> (30 g, 140.05 mmol) and (R)-2-methoxy-1-methyl-ethylamine (100 mL) was stirred at 65C for 2 days. A satured solution of NaHCU3 was added and the mixture was extracted with dichloromethane (3 times). The organic phase was washed twice with water then with brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane/ethyl acetate 9:1). The title compound (33.38 g, 84%) was obtained as oil.1 H-NMR (400 MHz), delta (ppm, DMSOd6): 7.87 (d, J=7.80 Hz, 1H), 7.80 (t, J=7.19 Hz, 1H), 6.60 (dd, J1 =13.05 Hz, J2=2.44 Hz, 1H), 6.36 (m, 1H), 3.80 (m, 1H), 3.40 (d, J=4.76 Hz, 2H), 3.30 (s, 3H), 1.53 (s, 9H), 1.17 (d, J=6.58 Hz, 3H).

Reference： [1]Patent: WO2010/69966,2010,A1 .Location in patent: Page/Page column 74

12
[ 636-76-0 ]
[ 37143-54-7 ]
[ 1094316-73-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 5637 - 5646

13
[ 1214344-87-2 ]
[ 37143-54-7 ]
[ 1563216-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 70℃;	184.1 Step 1: A mixture of 34-2 (1.5 g, 7.26 mmol), l -methoxypropan-2-amine (1.29 g, 14.5 mmol) and DMSO (10 mL) was stirred at 70°C overnight. Water was added and the resulting mixture was extracted with EA (30 mL x 3). The combined organic layers were washed with water and brine, dried over Na2SC>4 and evaporated. The residue was purified by column chromatography (eluent: PE to PE/EA = 100/1) to give 34B-1 as a colorless oil. JH NMR (301 MHz, CDC13) δ 7.75-7.74 (m, 1H), 7.54 (dd, / = 13.6, 1.9 Hz, 1H), 4.59 (s, 1H), 4.13-4.08 (m, 1H), 3.84 (s, 3H), 3.45-3.35 (m, 5H), 1.23 (d, / = 6.5 Hz, 3H). LC-MS: m/z = 276.0 [M+H]+.

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC. - WO2014/28669, 2014, A1 Location in patent: Paragraph 00659

14
[ 42237-85-4 ]
[ 37143-54-7 ]
[ 1562518-73-3 ]

Yield	Reaction Conditions	Operation in experiment
1.07 g	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; at 20℃;Cooling with ice;	Intermediate D5: (S)-3-Amino-5- pan-2-yl)benzamide. A stirred mixture of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (900 mg, 4.04 mmol), (S)-1- methoxypropan-2-amine (860 mu, 8.14 mmol) and triethylamine (1.7 mL, 12.20 mmol) in DCM (15 mL) was cooled in an ice bath. 50 wt% T3P in EtOAc (3.6 mL, 6.05 mmol) was added dropwise, the ice bath was removed and the reaction mixture allowed to warm to rt. DMF (2 mL) was added to aid solubility and the reaction stirred at rt overnight. The reaction mixture was partitioned between sat. aq. NaHC03 (50 mL) and DCM (50 mL). The aqueous phase was back extracted with fresh DCM (50 mL). The combined organic extracts were washed with water (100 mL), brine (100 mL), dried (MgS04), filtered and concentrated in vacuo to afford an orange oil. The crude product was purified by chromatography on silica gel (40 g column, 0-5% MeOH in DCM) to afford Intermediate D5 (1.07 g) as an orange oil. H NMR (DMSO-d6) 400 MHz, delta: 8.11 (d, 1 H), 7.08 (t, 1 H), 6.99-6.98 (m, 1 H), 6.84 (t, 1 H), 5.56 (s, 2H), 4.18-4.08 (m, 1 H), 3.39-3.35 (m, 1 H), 3.26-3.22 (m, 1 H), 3.25 (s, 3H), 1.09 (d, 3H). LCMS m/z 287/289 (M+H)+ (ES+)

Reference： [1]Patent: WO2014/27209,2014,A1 .Location in patent: Page/Page column 83

15
[ 20274-69-5 ]
[ 37143-54-7 ]
(S)-(4-((1-methoxypropan-2-yl)amino)-3-nitrophenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.4 g	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 120℃; for 0.5h;Microwave irradiation;	Intermediate 213: (S)-(4-((1-Methoxypropan-2-yl)amino)-3-nitrophenyl)methanol To a solution of <strong>[20274-69-5](4-fluoro-3-nitrophenyl)methanol</strong> (2 g, 11.69 mmol) in THF (10 mL) was added (S)- 1-methoxypropan-2-amine (1.851 mL, 17.53 mmol) and DIPEA (6.12 mL, 35.1 mmol) and the reaction mixture was heated under microwave conditions (initial high absorbtion setting) at 120 C for 30 min. The reaction mixture was partitioned between dichloromethane (3 x 150 mL) and saturated aqueous sodium bicarbonate solution (150 mL). The organic layers were combined, dried using a hydrophobic frit and evaporated under reduced pressure. The sample was loaded in dichloromethane and purified by SPE (silica, 100 g) using a gradient of 0-25 % EtOAc in cyclohexane. The appropriate fractions were combined and evaporated under reduced pressure to give the title compound (1.4 g, 5.83 mmol) as a orange gum. LCMS (System B): tRET = 0.82 min, MH+ = 241.

Reference： [1]Patent: WO2016/146738,2016,A1 .Location in patent: Page/Page column 105

16
[ 2105-96-6 ]
[ 37143-54-7 ]
(S)-4-((1-methoxypropan-2-yl)amino)-3-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		Intermediate 250: (S)-4-((1-methoxypropan-2-yl)amino)-3-nitrophenol A mixture of <strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (1.0 g, 6.37 mmol), (S)-1-methoxypropan-2-amine (1.13 g, 1.35 mL, 12.73 mmol) and diisopropylethylamine (1.65 g, 2.22 mL, 12.73 mmol) in dioxan (10 mL) was refluxed for 2 hours. The solvent was evaporated, the residue was dissolved in N-methyl-2- pyrrolidone (10 mL). The mixture was heated in a microwave at 180C for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate (50 mL) and water (25 mL). The organic phase was separated, washed with water (2x25 mL), dried and evaporated. The residue was chromatographed [10-40percent ethyl acetate/cyclohexane] to give the title compound (1.31 g, 5.79 mmol, 91 percent yield), as an orange solid. LCMS (System A): tRET = 0.89 min; MH+ 227.

Reference： [1]Patent: WO2016/146738,2016,A1 .Location in patent: Page/Page column 116-117

17
[ 37143-54-7 ]
[ 147808-42-2 ]
5-bromo-3-fluoro-N-[(2R)-1-methoxypropan-2-yl]-2-nitroaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium tert-butylate; In N,N-dimethyl-formamide; at 30℃; for 2h;	To a solution of (2R)-l-methoxypropan-2-amine (638 mg, 5.1 mmol) in DMF (15 mL) was added t-BuOK (1.08 g, 9.7 mmol). The mixture was stirred for 30 min. 5-bromo- l,3-difluoro-2-nitrobenzene (1.1 g, 4.6 mmol) was added and the reaction mixture was heated to 30C for 2 hr. It was then diluted with water (40 mL) and DCM (40 mL). The mixture was acidified to pH<6 by addition of AcOH. The organic layer was separated and the aquous one was extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (PE:EA = 30: 1 to 20: 1) to give the title compound (600 mg, 43%) as a brown solid. LCMS: 307; 309 (M+H)+.

Reference： [1]Patent: WO2016/168682,2016,A2 .Location in patent: Paragraph 0322

18
[ 6311-37-1 ]
[ 37143-54-7 ]
(S)-4-amino-3-bromo-N-(1-methoxypropan-2-yl)benzamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5790 - 5796

19
[ 17640-21-0 ]
[ 108-24-7 ]
[ 37143-54-7 ]
[ 437981-28-7 ]
(R)-2-methoxy-N-(1-methoxypropan-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: isopropyl methoxyacetate; methoxyisopropylamine With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction; Stage #2: acetic anhydride In ethanol; toluene at 60℃; enantioselective reaction;	4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up.

Reference： [1]Oláh, Márk; Kovács, Dániel; Katona, Gabriel; Hornyánszky, Gábor; Poppe, László [Tetrahedron, 2018, vol. 74, # 27, p. 3663 - 3670]

20
[ 17640-21-0 ]
[ 37143-54-7 ]
(R)-2-methoxy-N-(1-methoxypropan-2-yl)acetamide [ No CAS ]
(1S)-2-methoxy-1-methylethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With lipase B from Candida antarctica immobilized on acrylic beads In toluene at 30℃; for 8h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	4.4. Kinetic resolution of racemic amines rac-1a-i in shake flask General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 °C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up.

Reference： [1]Oláh, Márk; Kovács, Dániel; Katona, Gabriel; Hornyánszky, Gábor; Poppe, László [Tetrahedron, 2018, vol. 74, # 27, p. 3663 - 3670]

21
[ 14077-58-8 ]
[ 37143-54-7 ]
(±)-2-ethoxy-N-(1-methoxypropan-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With triethylamine In dichloromethane at 0 - 20℃; for 2h;	2.2. General method for preparation of racemic 2-alkoxyacetamides rac-3(a-d)(A-D) and rac-3(e-i)C General procedure: To a dry round-bottom flask was added a solution of the corresponding racemic amine (rac-1a-i, 0.5 mmol, 1.0 equiv.) and triethylamine (0.55 mmol, 1.1 equiv.) in dichloromethane (10 mL). This solution was cooled to 0 °C with ice bath and a solution of the corresponding 2-alkoxyacetyl chloride (9A-D; 0.5 mmol, 1. equiv.) in dichloromethane (10 mL) was added dropwise at 0 °C. The resulted mixture was stirred at 0 °C for 1 h and at RT for 1 h. The reaction mixtures was worked up and the crude product purified to afford the racemic 2-alkoxyacetamides rac-3(a-i)(A-D) as indicated in the following sections 2.2.1-2.2.4.

Reference： [1]Oláh, Márk; Kovács, Dániel; Katona, Gabriel; Hornyánszky, Gábor; Poppe, László [Tetrahedron, 2018, vol. 74, # 27, p. 3663 - 3670]

22
[ 110-91-8 ]
[ 4487-56-3 ]
[ 37143-54-7 ]
C₁₃H₂₀N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Starting material E-1.3.2 (500 mg; 2.46 mmol), (2S)-1 -methoxypropan-2-amine (219 mg; 2.46 mmol) and triethylamine (400 pl2.82 mmol) are suspended in 2.5 ml_ NMP and stirred for 1 h at 25 C. To this suspension morpholine (500 mI5.71 mmol) is added and the resulting mixture is stirred for 16 h at 50 C. The crude intermediate is purified using reversed phase chromatography (prep. HPLC1 ). This intermediate is dissolved in 30 ml_ THF and palladium on carbon is added. The reaction mixture is stirred for 3 h at 25 C and 4 bar hydrogen pressure. The solid material is filtered off and the solvent is evaporated. Yield: 65 % (422 mg; 1.59 mmol) HPLC-MS: (M+H)+ = 267; tRet = 0.59 min; method VAB

Reference： [1]Patent: WO2019/145410,2019,A1 .Location in patent: Page/Page column 20; 40

23
[ 5878-19-3 ]
[ 123-82-0 ]
[ 110-43-0 ]
[ 123-82-0 ]
[ 123-82-0 ]
[ 37143-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With disodium phosphate heptahydrate; disodium phosphite pentahydrate; In toluene; at 25℃; for 72h;Enzymatic reaction;	General procedure: In a dark glass vial (2 mL), immobilized EziG3-AsR-omegaTA (total mass 22 mg, 10% w w-1 enzymeloading to support material) and hydrate salt pair (Na2HPO3.5H2O/Na2HPO4.7H2O, total mass40 mg, 1:1, w w-1) were suspended in EtOAc (1 mL, at fixed aw of 0.7) and shaken for 15 min (900 rpm,thermomixer). The EziG3-AsR-TA was allowed to sediment and the solvent was removed bypipetting. The EziG3-AsR-omegaTA with hydrate salt pair was resuspended in another aliquot of EtOAc,and the above-described process was repeated twice. Next, the EziG3-AsR-omegaTA with hydrate salt pairwas washed with toluene (1 mL, at fixed aw of 0.7) and then allowed to sediment, after which thesolvent was removed by pipetting. Finally, toluene (1 mL total reaction volume, at fixed aw of 0.7) wasadded as a reaction solvent. The ketone substrate 1-3a (final concentration: 50 mM) and racemic aminedonor 4-6b (final concentration: 100 mM) were added, and the reaction vials were shaken in an uprightposition (900 rpm, thermomixer) for 72 h at 25 C. Work-up was performed by separating ketone and amine compounds from each other by extraction. First, the EziG3-AsR-omegaTA was left to sediment andthe organic reaction mixture was separated from the biocatalyst by pipetting. Then, naphthalene wasadded as an internal standard to the organic reaction mixture from a concentrated stock solution (50 muLfrom 1Mstock in toluene, final concentration 50 mM). The amine compounds were selectively extractedfrom the toluene reaction phase using an aqueous 2 M HCl solution (400 muL), thereby minimizingthe possible extraction of ketones. Following mixing and centrifugation (14 krpm, 5 min, 4 C),the two layers were separated and the organic layer was kept separate. The acidic aqueous layer wasre-extracted with toluene (2 x500 muL) to selectively remove potential traces of ketone. The organic layerswere combined and dried over MgSO4 prior to analysis. Then, the acidic aqueous layer-containingthe protonated amine products-was basified using an aqueous solution of either KOH (200 muL of a 10M stock solution) or K2CO3 (for reactions with substrate 2a), and extracted with EtOAc containing50 mM naphthalene as an internal standard (2 x 500 muL). Drying over MgSO4 was performed priorto analysis. Analysis was performed by separately injecting ketone- and amine-containing solutionson GC equipped with an achiral column (see Section 4.6 for details on analytical equipment anddetermination). For the determination of enantiomeric excess, the samples containing amines werederivatized by incubation with 4-dimethylaminopyridine in acetic anhydride (final concentration:5 mg mL-1) for 30 min (170 rpm, RT). Samples were quenched by the addition of water (500 L) andshaken for 30 min (170 rpm, RT). Following centrifugation, the organic layer was dried over MgSO4and analyzed by GC equipped with a chiral column (see Section 4.6 for details on analytical equipmentand determination).

Reference： [1]Molecules,2020,vol. 25

24
[ 3121-61-7 ]
[ 37143-54-7 ]
C₁₀H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetrabutylammoniun azide In acetonitrile at 25 - 26℃; for 20h; Sealed tube; Irradiation;

Reference： [1]Alder, Catherine M.; Ballantyne, George; Cresswell, Alexander J.; Cunningham, William B.; Edwards, Lee J.; Grayson, Matthew N.; Kinsella, Anna G.; McKay, Blandine S. J.; Mules, Tom; Ryder, Alison S. H.; Turner-Dore, Jacob [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 14986 - 14991][Angew. Chem., 2020, vol. 132, # 35, p. 15096 - 15101,6]

25
[ 682-30-4 ]
[ 37143-54-7 ]
(RS)-diethyl (3-amino-4-methoxy-3-methylbutyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetrabutylammoniun azide In acetonitrile at 25 - 26℃; for 20h; Irradiation;	4.2 General Procedure 1 for α-C-H alkylation of primary amines 8 with diethyl vinylphosphonate 9 General procedure: A 20-mL scintillation vial equipped with a stirrer bar was transferred to a nitrogen-filled purge box. In the case of solid or viscous oil amine substrates, the requisite amine 8 (0.45 mmol, 1.0 equiv) was then weighed into the empty vial at this point, and the stirrer bar replaced. The vial was then charged with stock solutions of the 4CzIPN (2.28 mM in MeCN, 1.97 mL, 4.5 μmol, 1 mol%) and tetrabutylammonium azide (70.3 mM in MeCN, 640 μL, 45 μmol, 10 mol%), and made up to a total volume of 3.0 mL by addition of MeCN. For liquid amines, the requisite amine (0.45 mmol, 1.0 equiv) was then transferred into the vial by microlitre syringe at this point. Finally, diethyl vinylphosphonate 9 (70 μL, 74 mg, 0.45 mmol, 1.0 equiv) was added, and the vial was sealed using a B24 rubber septa. It was then removed from the purge box and transferred to a photoreactor, and irradiated (with stirring) for 20 h at 425 nm. Fan cooling was used to maintain an external temperature of 25-26 °C. Following irradiation, the reaction mixture was concentrated in vacuo.

Reference： [1]Grayson, James D.; Cresswell, Alexander J. [Tetrahedron, 2021, vol. 81]

26
[ 1300031-57-5 ]
[ 37143-54-7 ]
7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-4-((1-methoxypropan-2-yl)amino)quinoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
116 mg	With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 8h;

Reference： [1]Jones, Katherine L.; Beaumont, Dominic M.; Bernard, Sharon G.; Bit, Rino A.; Campbell, Simon P.; Chung, Chun-Wa; Cutler, Leanne; Demont, Emmanuel H.; Dennis, Kate; Gordon, Laurie; Gray, James R.; Haase, Michael V.; Lewis, Antonia J.; McCleary, Scott; Mitchell, Darren J.; Moore, Susanne M.; Parr, Nigel; Robb, Olivia J.; Smithers, Nicholas; Soden, Peter E.; Suckling, Colin J.; Taylor, Simon; Walker, Ann L.; Watson, Robert J.; Prinjha, Rab K. [Journal of Medicinal Chemistry, 2021, vol. 64, # 16, p. 12200 - 12227]

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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
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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.
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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.
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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
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P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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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.
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P332	IF SKIN irritation occurs:
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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
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P401
P402	Store in a dry place.
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P413
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P422
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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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Physical hazards
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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
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H226	Flammable liquid and vapour
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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
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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
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H351	Suspected of causing cancer
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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

[ CAS No. 37143-54-7 ] {[proInfo.proName]}

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[ 37143-54-7 ] Synthesis Path-Downstream 1~26

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