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tert-Butyl cyanoacetate

tert-Butyl cyanoacetate structure

CAS No:
1116-98-9
Formula:
C7H11NO2
Chemical Name:
tert-Butyl cyanoacetate
Synonyms:
Acetic acid,2-cyano-,1,1-dimethylethyl ester;Acetic acid,cyano-,tert-butyl ester;Acetic acid,cyano-,1,1-dimethylethyl ester;tert-Butyl cyanoacetate;1,1-Dimethylethyl cyanoacetate;Cyanoacetic acid tert-butyl ester;NSC 1072;tert-Butyl 2-cyanoacetate;tert-Butyl α-cyanoacetate;57710-63-1;1654002-83-1
Categories:
Organic Chemistry > Carboxylic Acids and Derivatives

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tert-Butyl cyanoacetate Basic Attributes

Molecular Weight：

141.17

Exact Mass：

141.17

BRN：

1755933

EC Number：

214-243-7

UNII：

PWT31M9VDL

NSC Number：

1072

DSSTox ID：

DTXSID8061501

HScode：

2926909090

Characteristics

PSA：

50.1

XLogP3：

Appearance：

colorless liquid

Density：

1.0095 g/cm³ @ Temp: 21 °C

Melting Point：

107-108ºC

Boiling Point：

90 °C @ Press: 10 Torr

Flash Point：

91°C

Refractive Index：

1.426

Storage Conditions：

2-8°C

Vapor Pressure：

0.003mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

24/25

Marks：

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory.

tert-Butyl cyanoacetate Use and Manufacturing

Methods of Manufacturing

Under argon, cyanoacetic acid (7.16 mmol) and t-butanol (6.51 mmol) are dissolved in anhydrous dichloromethane (30 mL) and cooled to 0° C. DCC (7.16 mmol) and DMAP (cat.) are added to the solution. The medium is stirred for 4 hours at 0° C. and 1 h at room temperature. The reaction mixture is filtered, then concentrated under reduced pressure. The thereby obtained is purified by column chromatography (SiOCyanoacetic acid (1.705 g, 20 mmol) was dissolved in 20 mL acetonitrile. Tert-butyl alcohol (2.7 mL, 28 mmol) was added dropwise to the mixture under stirring at 25 °C. Then 24 mL of 1 M acetonitrile solution of DCC was added through a dropping funnel carefully. The reaction mixture was stirred for an additional 5 h and filtered through a sintered glass. Upon evaporation of the solvents, the reaction mixture was purified by flash column chromatography (silica gel, petroleum ether: ethyl acetate, 10:1) to afford the product (2.365 g, 84percent yield) as colourless oil. (Z) -2- cyano-3-ethoxy-acrylate, t-butyl ester: cyanide acid containing 5 g (0.059 mole) and 5.2 g tertiary butyl alcohol (0.07 mmol, 1.2 equiv.) In acetonitrile / methanol (1: 1) was added portionwise at 0 12 g N, N'- dicyclohexyl carbodiimide (0.059 mole, 1 eq.) and stirred for 20 minutes, the reaction mixture was filtered, the organic layer was concentrated in a vacuum concentrator, after to give a yellow oil was purified by flash column chromatography on silica gel (petroleum ether / ethyl acetate = 10/1) to obtain 5.4 g of tert-butyl cyanoacetate (yield: 65percent). 200 ml of acetic anhydride was added to a solution containing 13.5 g of tert-butyl cyanoacetate (0.0957 mmol) in 17 g of triethoxymethane (0.115 mmol, 1.2 eq.), The reaction mixture was heated to reflux for fifteen hours, The solvent was removed in vacuo and then down a red oil (16 g, 85percent).t-Butanol (1.86 ml, 19.40 mmol, 1.1 eq) was mixed with cyanoacetic acid 7a (1.5 g, 17.63 mmol, 1 eq) in dry dichloromethane (30 ml). DCC (3.64 g, 17.63 mmol, 1 eq) was added dropwise. After stirring at room temperature for 18h, the white solid was filtrated and the resulting solution was concentrated in vacuo. Chromatography purification of the residue on silica gel with 9 cyclohexane/1 Ethyl acetate gave the desired ester 8k as a pale liquid (1.13 g, 45percent).

Manufacturing Info：

Acetic acid, 2-cyano-, 1,1-dimethylethyl ester: INACTIVE

Computed Properties

Molecular Weight:141.17
XLogP3:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:141.078978594
Monoisotopic Mass:141.078978594
Topological Polar Surface Area:50.1
Heavy Atom Count:10
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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