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67843-74-7

Basic Information
CAS No.: 67843-74-7
Name: (S)-(+)-Epichlorohydrin
Article Data: 77
Molecular Structure:
Molecular Structure of 67843-74-7 ((S)-(+)-Epichlorohydrin)
Formula: C3H5ClO
Molecular Weight: 92.5251
Synonyms: Oxirane,(chloromethyl)-, (2S)- (9CI);Oxirane, (chloromethyl)-, (S)-;(+)-2-(Chloromethyl)oxirane;(+)-Epichlorohydrin;(S)-(Chloromethyl)oxirane;(S)-1-Chloro-2,3-epoxypropane;(S)-2-Chloromethyloxirane;BRN 1420784;(S)-Epichlorohydrin;2(S)-Epichlorohydrin;
EINECS: 203-439-8
Density: 1.205 g/cm3
Melting Point: 57 °C(lit.)
Boiling Point: 116.1 °C at 760 mmHg
Flash Point: 33.9 °C
Solubility: Insoluble in water
Appearance: Colorless to light yellow liquid
Hazard Symbols: ToxicT
Risk Codes: 45-10-23/24/25-34-43
Safety: 53-45
Transport Information: UN 2023 6.1/PG 2
PSA: 12.53000
LogP: 0.62400
Synthetic route
96-23-1

1,3-Dichloro-2-propanol

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC mutant P175S/W249P) In aq. phosphate buffer pH=8; Concentration; Reagent/catalyst; Temperature; pH-value; Solvent; Enzymatic reaction; enantioselective reaction;93.7%
With halohydrin dehalogenase mutant HheCPS F86N In aq. phosphate buffer at 37℃; pH=8; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;79.12%
3132-64-7

1,2-Epoxy-3-bromopropane

A

67843-74-7

(S)-epichlorohydrin

B

14437-88-8

(2R)-3-bromo-1,2-propanediol

Conditions
ConditionsYield
With (R,R)-Jacobsen catalyst; water In tetrahydrofuran at 4℃; for 24h;A n/a
B 93%
621-84-1

O-benzyl carbamate

106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

641617-19-8

[(R)-3-chloro-2-hydroxypropyl]carbamic acid benzyl ester

Conditions
ConditionsYield
With air; 4-nitro-benzoic acid; (R,R)-((t-Bu)4-salen)Co(II) In various solvent(s) at 0℃; for 24h;A n/a
B 87%
67800-61-7

(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With sodium ethane-1,2-diolate In ethylene glycol for 0.25h; Ambient temperature;85%
106-89-8

epichlorohydrin

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With water; [(1-RR)-(Dibenzoyl-LTA)] at 5 - 20℃; for 7h; Product distribution / selectivity; Industry scale; Resolution of racemate;82%
With water; [(1-RR)-(Dibenzoyl-LTA)] at 5 - 20℃; for 3h; Product distribution / selectivity; Resolution of racemate;80%
With oligomeric (salen)Co(OSO2CF3); water at 20℃; for 15h;44%
67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With sodium hydroxide74%
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

57090-45-6

(2R)-3-chloro-1,2-propanediol

Conditions
ConditionsYield
With C72H102Co2F12N4O12P2; water at 0 - 20℃; for 3h; optical yield given as %ee;A 45%
B 53%
With water; (S,S)-(salen)cobalt(III)(OAc) at 0℃; for 19h;A 46%
B 45%
With C114H155Co3N8O14Pol; water; acetic acid at 20℃; for 3h; Resolution of racemate; optical yield given as %ee; enantioselective reaction;A 46%
B n/a

(S)-1,3-dichloro-1-propanol

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With potassium hydroxide In methanol Ambient temperature;51%
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

57090-45-6

(2R)-3-chloro-1,2-propanediol

C

60827-45-4

(S)-3-chloropropan-1,2-diol

Conditions
ConditionsYield
With water; dimeric chiral (salen)Co complex linked with Al at 20℃; for 5h; Product distribution; Further Variations:; Catalysts;A 46%
B n/a
C n/a
With water; Cr(III)-endo,endo-2,5-diaminonorbornane-salen In tetrahydrofuran at 20℃; for 42h;A 46%
B n/a
C n/a
With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate; water In dichloromethane; acetonitrile at 20℃; for 11h;A 45%
B n/a
C n/a
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

96-24-2

3-monochloro-1,2-propanediol

Conditions
ConditionsYield
Stage #1: epichlorohydrin With C57H54CoN3O8 In dichloromethane at 20℃; for 0.25h;
Stage #2: With water In dichloromethane at 20℃; for 12h; Cooling with ice; enantioselective reaction;
A 46%
B n/a
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Specification

The (S)-(+)-Epichlorohydrin with CAS registry number of 67843-74-7 is also known as Oxirane, (chloromethyl)-, (S)-. The IUPAC name is (2S)-2-(Chloromethyl)oxirane. It belongs to product categories of Industrial/Fine Chemicals; Chiral; Chiral Compounds; Chiral Building Blocks; Glycidyl Compounds, etc. (Chiral); Oxiranes; Simple 3-Membered Ring Compounds; Synthetic Organic Chemistry. Its EINECS registry number is 203-439-8. In addition, the formula is C3H5ClO and the molecular weight is 92.52. This chemical is a colorless to light yellow liquid and should be stored in sealed containers away from acid, alkali, metal alloy and oxidizing agents.

Physical properties about (S)-(+)-Epichlorohydrin are: (1)ACD/LogP: 0.45; (2)ACD/LogD (pH 5.5): 0.45; (3)ACD/LogD (pH 7.4): 0.45; (4)ACD/BCF (pH 5.5): 1.29; (5)ACD/BCF (pH 7.4): 1.29; (6)ACD/KOC (pH 5.5): 41.84; (7)ACD/KOC (pH 7.4): 41.84; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.443; (11)Molar Refractivity: 20.37 cm3; (12)Molar Volume: 76.7 cm3; (13)Surface Tension: 35.6 dyne/cm; (14)Density: 1.205 g/cm3; (15)Flash Point: 33.9 °C; (16)Enthalpy of Vaporization: 33.98 kJ/mol; (17)Boiling Point: 116.1 °C at 760 mmHg; (18)Vapour Pressure: 22 mmHg at 25 °C.

Preparation of (S)-(+)-Epichlorohydrin: it is prepared by reaction of (S)-2,3-dichloropropanol. The reaction needs reagent KOH and solvent methanol at ambient temperature. The yield is about 51%.

(S)-(+)-Epichlorohydrin is prepared by reaction of (S)-2,3-dichloropropanol.

Uses of (S)-(+)-Epichlorohydrin: it is used to produce (S)-1-chloro-2-heptanol by reaction with butylmagnesium bromide. The reaction occurs with reagent CuBr2*SMe and solvents diethyl ether, tetrahydrofuran at -30 °C for 5 hours. The yield is about 60%.

(S)-(+)-Epichlorohydrin is used to produce (S)-1-chloro-2-heptanol by reaction with butylmagnesium bromide.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic by inhalation, in contact with skin and if swallowed. It may cause burns, sensitisation by skin contact and even cancer. Besides, it is flammable. During using it, obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1C(O1)CCl
2. Isomeric SMILES: C1[C@H](O1)CCl
3. InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
4. InChIKey: BRLQWZUYTZBJKN-GSVOUGTGSA-N