(S)-(-)-Methyl 2-chloropropionate supplier

Name
(S)-(-)-Methyl 2-chloropropionate
EINECS 412-470-8
CAS No. 73246-45-4
Article Data14
CAS DataBase
Density 1.116 g/cm³
Solubility
Melting Point
Formula C₄H₇ClO₂
Boiling Point 130.8 °C at 760 mmHg
Molecular Weight 122.551
Flash Point 37.6 °C
Transport Information UN 2933 3/PG 3
Appearance Colorless liquid
Safety 23-26-36
Risk Codes 10-36-48/22
Molecular Structure
Hazard Symbols Xn
Synonyms Propanoicacid, 2-chloro-, methyl ester, (S)-;(-)-2-Chloropropionic acid methyl ester;(-)-Methyl 2-chloropropanoate;(-)-Methyl 2-chloropropionate;(-)-Methyl a-chloropropionate;(S)-(-)-2-Chloropropionic acid methyl ester;(S)-2-Chloropropanoic acid methylester;(S)-2-Chloropropionic acid methyl ester;(S)-Methyl 2-chloropropionate;L-a-Chloropropionic acid methylester;Methyl (S)-(-)-2-chloropropionate;Methyl (S)-2-Chloropropanoate;Methyl(S)-a-chloropropionate;MethylL-(-)-2-chloropropionate;Methyl l-a-chloropropionate;
PSA 26.30000
LogP 0.78670

Synthetic route

: 17392-83-5
(R)-Methyl lactate

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With pyridine; thionyl chloride In N,N-dimethyl-formamide at 20 - 55℃; for 5h; Temperature; Reagent/catalyst; Solvent;	90%

: 17392-83-5
(R)-Methyl lactate

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 77287-29-7
methyl (2R)-2-chloropropanoate

Conditions

Conditions	Yield
With pyridine; thionyl chloride In N,N-dimethyl-formamide at 20 - 55℃; for 6h;	A 86% B n/a

: 27871-49-4
(S)-Methyl lactate

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With thionyl chloride at 100℃;	75%
With thionyl chloride In diethyl ether at 20℃; for 16h;	72%

: 67-56-1
methanol

: 29617-66-1
(S)-2-chloropropanoic acid

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 5h; Reflux;	66%
With boron trifluoride
With thionyl chloride optical yield given as %ee;	124 mg

: 186581-53-3, 908094-01-9
diazomethane

: 29617-66-1
(S)-2-chloropropanoic acid

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With hexane

: 67-56-1
methanol

: 79-33-4
L-Lactic acid

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With phosphorus pentachloride methyl ester of/the/ l-α-chloro-propionic acid;

: 67-56-1
methanol

: 70110-24-6
(S)-2-chloropropionyl chloride

: 73246-45-4
methyl-(S)-2-chloropropionate

: 17392-83-5
(R)-Methyl lactate

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 20047-41-0, 57885-43-5, 5445-17-0, 62076-23-7
methyl (2S)-2-bromopropanoate

Conditions

Conditions	Yield
With pyridine; thionyl chloride; hydrogen bromide Yield given. Multistep reaction. Yields of byproduct given;

: 77287-29-7
methyl (2R)-2-chloropropanoate

: 73246-45-4
methyl-(S)-2-chloropropionate

Conditions

Conditions	Yield
With N,N,N',N',N'',N''-hexamethylguanidinium chloride at 70℃; Product distribution; Further Variations:; Temperatures; Reagents;

: methyl S-(-)-2-(chlorocarbonyloxy)propionate

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 77287-29-7
methyl (2R)-2-chloropropanoate

Conditions

Conditions	Yield
With N,N,N',N',N'',N''-hexamethylguanidinium chloride at 70℃; Product distribution; Further Variations:; Temperatures; Reagents;

: 7474-05-7
(R)-2-chloropropionic acid

: 18107-18-1
diazomethyl-trimethyl-silane

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 77287-29-7
methyl (2R)-2-chloropropanoate

Conditions

Conditions	Yield
In methanol; hexane; toluene for 0.0833333h; Title compound not separated from byproducts;

...Expand

: 17639-93-9
2-chloro-propionic acid methyl ester

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 77287-29-7
methyl (2R)-2-chloropropanoate

Conditions

Conditions	Yield
With poly{N-[(1S,2S)-2-benzyloxycyclopentyl]maleimide} Resolution of racemate;

: 80-63-7
methyl 2-chloroacrylate

A: 73246-45-4
methyl-(S)-2-chloropropionate

B: 77287-29-7
methyl (2R)-2-chloropropanoate

Conditions

Conditions	Yield
With Saccharomyces cerevisiae Old Yellow Enzyme 3 ene-reductase; nicotinamine adenine dinucleotide at 30℃; for 24h; pH=7.5; aq. buffer; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;

: 73246-45-4
methyl-(S)-2-chloropropionate

: 123-31-9
hydroquinone

: 96562-58-2
(R)-(+)-2-(4-hydroxyphenoxy)propionic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; for 3h; Temperature;	95%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 10387-40-3
potassium thioacetate

: 33302-03-3
methyl (2R)‐2‐(acetylthio)propanoate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	94.8%
In acetone

: 73246-45-4
methyl-(S)-2-chloropropionate

: 106-48-9
4-chloro-phenol

: 3307-39-9, 20421-33-4, 20421-35-6, 20421-34-5
(R)-2-(4-chlorophenoxy)propanoic acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-phenol With potassium hydroxide In water at 60℃; for 0.5h; Stage #2: methyl-(S)-2-chloropropionate In water at 60℃; for 4h; Reagent/catalyst;	92.2%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 56827-86-2
cesium thioacetate

: (S)-methyl 2-(acetylsulfanyl)propionate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃;	89%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 507-09-5
thioacetic acid

: 33302-03-3
methyl (2R)‐2‐(acetylthio)propanoate

Conditions

Conditions	Yield
Stage #1: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl-(S)-2-chloropropionate In N,N-dimethyl-formamide for 3h;	88%
Stage #1: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: methyl-(S)-2-chloropropionate In N,N-dimethyl-formamide at 20℃; for 1h;	82%
Stage #1: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: methyl-(S)-2-chloropropionate In N,N-dimethyl-formamide at 20℃; for 1h;	82%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 7328-91-8
2,2-Dimethyl-1,3-diaminopropane

: dimethyl 2,2'-((2,2-dimethylpropane-1,3-diyl)bis(azanediyl))(2R,2'R)-dipropionate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	85.9%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 86-74-8
9H-carbazole

: C16H15NO2

Conditions

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 25℃; for 1.5h; Inert atmosphere; Stage #2: methyl-(S)-2-chloropropionate In N,N-dimethyl-formamide; mineral oil at 25℃; for 12h; Inert atmosphere;	84%

: 2075-45-8
4-bromo-1H-pyrazole

: 73246-45-4
methyl-(S)-2-chloropropionate

: 877399-68-3
2-(4-bromo-pyrazol-1-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 4-bromo-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Stage #2: methyl-(S)-2-chloropropionate In N,N-dimethyl-formamide for 4h;	77%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 5-(3-(3-ethyl-4-(2-(piperidin-4-yl)ethoxy)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-3-(trifluoromethyl)picolinonitrile hydrochloride

: (R)-methyl 2-(4-(2-(4-(3-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-ethylphenoxy)ethyl)piperidin-1-yl)propanoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 85℃; for 48h;	76%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 185223-00-1
[(Ir(μ-pyrazolate)(CNBu(t))2)2]

: 203636-13-9, 315178-95-1
(+/-)-[(CNBu-t)2(Cl)Ir(μ-pyrazolato)2Ir(η1-CH(Me)CO2Me)(CNBu-t)2]

Conditions

Conditions	Yield
In benzene CH3CO2CH(CH3)Cl was added to a soln. of complex in benzene, 30 min in the dark (Ar); the soln. was layered with hexane, allowed to stand 2 d in the darkness, crystals were sepd. by decantation, washed with cold hexane and vac.-dried; elem. anal.;	65%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 1645-76-7
hexafluoroacetone oxime

: 213010-46-9
(R)-2-(2,2,2-Trifluoro-1-trifluoromethyl-ethylideneaminooxy)-propionic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile 1) 0-5 deg C, 10 h; 2) 20 deg C, 10 h;	64%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 55697-53-5
methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

A: 177421-03-3
(R)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-propionic acid methyl ester

B: 177421-02-2
(S)-2-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-propionic acid methyl ester

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 60 deg C, 1 h, 2.) 60 deg C, 24 h;	A 8.4% B 57.2%

...Expand

: 75-15-0
carbon disulfide

: 73246-45-4
methyl-(S)-2-chloropropionate

: 63126-47-6, 76946-27-5, 84025-81-0, 135523-48-7
(2R)-methoxymethylpyrrolidine

: 2(R)-((R)-2-Methoxymethylpyrrolidin-1-ylthiocarbonylthio)-propansaeuremethylester

Conditions

Conditions	Yield
With sodium acetate In methanol	56.8%

...Expand

: 73246-45-4
methyl-(S)-2-chloropropionate

: 4-(3-(3-chloro-4-(2-(piperazin-1-yl)ethoxy)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile hydrochloride

: (R)-methyl 2-(4-(2-(2-chloro-4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)phenoxy)ethyl)piperazin-1-yl)propanoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃; for 6h;	48.4%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 4-(3-(3-ethyl-4-(2-(piperidin-4-yl)ethoxy)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

: 76-05-1
trifluoroacetic acid

: (R)-methyl 2-(4-(2-(4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-ethylphenoxy)ethyl)piperidin-1-yl)propanoate trifluoroacetate

Conditions

Conditions	Yield
Stage #1: methyl-(S)-2-chloropropionate; 4-(3-(3-ethyl-4-(2-(piperidin-4-yl)ethoxy)phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile With triethylamine In tetrahydrofuran at 85℃; for 48h; Stage #2: trifluoroacetic acid In acetonitrile	47.5%

...Expand

: 75-15-0
carbon disulfide

: 73246-45-4
methyl-(S)-2-chloropropionate

: 63126-47-6
(2S)-2-(methoxymethyl)-1-pyrrolidine

: 2(R)-((S)-2-Methoxymethylpyrrolidin-1-ylthiocarbonylthio)-propansaeuremethylester

Conditions

Conditions	Yield
With sodium acetate In methanol	47.3%

...Expand

: 73246-45-4
methyl-(S)-2-chloropropionate

: 3-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenol

: methyl (R)-2-(3-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenoxy)propanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	39%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 141-43-5
ethanolamine

: 13882-80-9
2-methyl-morpholin-3-one

Conditions

Conditions	Yield
With sodium In 1,4-dioxane for 3h; Reflux;	14.2%

: 73246-45-4
methyl-(S)-2-chloropropionate

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 104891-12-5
(+)-SC,RS-3-chloro-1-(4-methylphenyl)sulphinyl-2-butanone

: 73246-45-4
methyl-(S)-2-chloropropionate

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: (2S,2'R)-dimethyl 3-phenyl-2,2'-iminodipropionate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 80 - 100℃; for 48h;

: 73246-45-4
methyl-(S)-2-chloropropionate

: 555-31-7
aluminum isopropoxide

: 40058-87-5
iso-propyl-2-chloropropanoate

Conditions

Conditions	Yield
at 25℃; Product distribution; also with titanium isopropoxide;

: 73246-45-4
methyl-(S)-2-chloropropionate

A: 67-56-1
methanol

B: 29617-66-1
(S)-2-chloropropanoic acid

Conditions

Conditions	Yield
subtilisin In water at 30℃; Kinetics;
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; esterase from Pseudomonas fluorescens In water at 25℃; pH=7.20; Enzyme kinetics;
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics;
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;

(S)-(-)-Methyl 2-chloropropionate Specification

The (S)-(-)-Methyl 2-chloropropionate, with the CAS registry number 78341-97-6, is also known as (S)-(-)-2 Chloropropionic acid methyl ester. It belongs to the product categories of Categories: chiral; Chiral Compounds; Chiral Building Blocks; Esters (Chiral); Synthetic Organic Chemistry; Chiral Building Blocks; Esters; Organic Building Blocks. Its EINECS number is 412-470-8. This chemical's molecular formula is C₄H₇ClO₂ and molecular weight is 122.55. What's more, its systematic name is Methyl (2S)-2-chloropropanoate. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, heat and fire.

Physical properties of (S)-(-)-Methyl 2-chloropropionate are: (1)ACD/LogP: 0.872; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.87; (4)ACD/LogD (pH 7.4): 0.87; (5)ACD/BCF (pH 5.5): 2.71; (6)ACD/BCF (pH 7.4): 2.71; (7)ACD/KOC (pH 5.5): 71.03; (8)ACD/KOC (pH 7.4): 71.03; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.409; (14)Molar Refractivity: 27.163 cm³; (15)Molar Volume: 109.806 cm³; (16)Polarizability: 10.768×10^-24cm³; (17)Surface Tension: 27.67 dyne/cm; (18)Density: 1.116 g/cm³; (19)Flash Point: 37.601 °C; (20)Enthalpy of Vaporization: 36.838 kJ/mol; (21)Boiling Point: 130.759 °C at 760 mmHg; (22)Vapour Pressure: 9.57 mmHg at 25°C.

Preparation of (S)-(-)-Methyl 2-chloropropionate: this chemical can be prepared by (S)-2-hydroxy-propionic acid methyl ester at the temperature of 20 °C. This reaction will need reagent SOCl₂ and solvent diethyl ether with the reaction time of 16 hours. The yield is about 72%.

(S)-(-)-Methyl 2-chloropropionate can be prepared by (S)-2-hydroxy-propionic acid methyl ester at the temperature of 20 °C

Uses of (S)-(-)-Methyl 2-chloropropionate: it can be used to produce (S)-methyl 2-(acetylsulfanyl)propionate at the temperature of 25 °C. It will need solvent dimethylformamide. The yield is about 89%.

(S)-(-)-Methyl 2-chloropropionate can be used to produce (S)-methyl 2-(acetylsulfanyl)propionate at the temperature of 25 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is flammable and is irritating to eyes. This substance is harmful as it has a danger of serious damage to health by prolonged exposure if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). When using it, you need to wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl[C@H](C(=O)OC)C
(2)Std. InChI: InChI=1S/C4H7ClO2/c1-3(5)4(6)7-2/h3H,1-2H3/t3-/m0/s1
(3)Std. InChIKey: JLEJCNOTNLZCHQ-VKHMYHEASA-N

Product Name

(S)-(-)-Methyl 2-chloropropionate

Synthetic route

(S)-(-)-Methyl 2-chloropropionate Specification

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