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75885-58-4

Basic Information
CAS No.: 75885-58-4
Name: (S)-(+)-2,2-Dimethylcyclopropanecarboxamide
Article Data: 9
Molecular Structure:
Molecular Structure of 75885-58-4 ((S)-(+)-2,2-Dimethylcyclopropanecarboxamide)
Formula: C6H11NO
Molecular Weight: 113.159
Synonyms: Cyclopropanecarboxamide,2,2-dimethyl-, (S)-;(+)-2,2-Dimethylcyclopropanecarboxamide;(S)-2,2-Dimethylcyclopropanecarboxamide;S-(+)-2,2-Dimethylcyclopropane-1-carboxamide;
EINECS: 278-334-3
Density: 1.028 g/cm3
Melting Point: 135-137 °C(lit.)
Boiling Point: 225.1 °C at 760 mmHg
Flash Point: 89.933 °C
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 43.09000
LogP: 1.21810
Synthetic route
14590-53-5

(+)-1S-2,2-dimethylcyclopropane-carboxylic acid

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
Stage #1: (+)-1S-2,2-dimethylcyclopropane-carboxylic acid With thionyl chloride In dichloromethane at 20℃;
Stage #2: With ammonia In dichloromethane at -15℃;
92.1%
Multi-step reaction with 2 steps
1: 93 percent / pyridine / 1.5 h / Ambient temperature
2: 83 percent / 3 M NH3 / ethanol / 0.75 h
View Scheme
89007-61-4

(S)-ethyl 2,2-dimethylcyclopropanecarboxylate

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With thionyl chloride; ammonia In dichloromethane90.7%
With ammonia; calcium chloride In methanol at 100 - 110℃;10 g
107871-21-6

(+)-N-<<(2,2-dimethylcyclopropyl)carbonyl>oxy>succinimide

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With ammonium hydroxide In ethanol for 0.75h;83%
220263-88-7

2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanone

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With aminolysis72%
1759-55-3

(RS)-2,2-dimethylcyclopropanecarboxamide

A

28624-52-4

(R)-2,2-dimethylcyclopropanecarboxylic acid

B

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With water In acetonitrile at 30℃; for 2.33333h; pH=8.2; Solvent; Concentration; Enzymatic reaction; enantioselective reaction;A n/a
B 43.5%
With R-amidase from Delftia tsuruhatensis CCTC M 205114 at 35℃; for 18h; Large scale reaction; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;A n/a
B 34.2%
645413-67-8

2,2-dimethylcyclopropane carboxylic acid 2,2,2-trifluoroethyl ester

A

C8H11F3O2

B

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30 - 40℃; for 20h; Product distribution / selectivity; Enzymatic reaction;A n/a
B 40%
220263-87-6

(R)-2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanol

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / Na2Cr2O7, H2SO4 / acetic acid
2: 72 percent / aminolysis
View Scheme
75885-59-5

2,2-dimethylcyclopropane-1-carboxylic acid

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 93 percent / pyridine / 1.5 h / Ambient temperature
3: 83 percent / 3 M NH3 / ethanol / 0.75 h
View Scheme

C9H16O3

A

C9H16O3

B

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30℃; for 20h; Product distribution / selectivity; Enzymatic reaction;A n/a
B n/a

C8H13BrO2

A

C8H13BrO2

B

75885-58-4

(S)-2,2-dimethylcyclopropanecarboxamide

Conditions
ConditionsYield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30℃; for 20h; Product distribution / selectivity; Enzymatic reaction;A n/a
B n/a
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Chemistry

Molecular Structure of Cyclopropanecarboxamide,2,2-dimethyl-, (1S)- (CAS NO.75885-58-4):

IUPAC Name: (1S)-2,2-dimethylcyclopropane-1-carboxamide 
Empirical Formula: C6H11NO
Molecular Weight: 113.1576 
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 43.09 Å2
Index of Refraction: 1.48
Molar Refractivity: 31.264 cm3
Molar Volume: 110.074 cm3
Surface Tension: 36.109 dyne/cm
Density: 1.028 g/cm3
Flash Point: 89.933 °C
Enthalpy of Vaporization: 46.161 kJ/mol
Boiling Point: 225.092 °C at 760 mmHg
Vapour Pressure: 0.088 mmHg at 25°C
Melting point: 135-137 °C(lit.)
EINECS: 278-334-3
Product Categories: AMIDE; Amides; Chiral Compounds; chiral; API intermediates; API; Amides (Chiral); Chiral Building Blocks; Cyclopropanes; Simple 3-Membered Ring Compounds; Synthetic Organic Chemistry; Chiral Compound; Chiral Building Blocks; Organic Building Blocks

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant

Specification

 Cyclopropanecarboxamide,2,2-dimethyl-, (1S)- , with CAS number of 75885-58-4, can be called Cyclopropanecarboxamide, 2,2-dimethyl-, (S)- ; (+)-2,2-Dimethylcyclopropanecarboxamide ; S-(+)-2,2-Dimethylcyclopropane-1-carboxamide ; (S)-2,2-Dimethylcyclopropanecarboxamide . It is a white to light yellow crystal powde.