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

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide Synthetic route

: 14590-53-5
(+)-1S-2,2-dimethylcyclopropane-carboxylic acid

: 75885-58-4
(S)-2,2-dimethylcyclopropanecarboxamide

Conditions

Conditions	Yield
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

Conditions	Yield
With thionyl chloride; ammonia In dichloromethane	90.7%
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

Conditions	Yield
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

Conditions	Yield
With aminolysis	72%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide Chemical Properties

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

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
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

(S)-(+)-2,2-Dimethylcyclopropanecarboxamide 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.

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