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tert-Butyl cyanoacetate

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Name

tert-Butyl cyanoacetate

EINECS 214-243-7
CAS No. 1116-98-9 Density 1.001 g/cm3
PSA 50.09000 LogP 1.24178
Solubility N/A Melting Point 107-108oC
Formula C7H11NO2 Boiling Point 194.6 °C at 760 mmHg
Molecular Weight 141.17 Flash Point 79 °C
Transport Information N/A Appearance colorless liquid
Safety 24/25 Risk Codes 22
Molecular Structure Molecular Structure of 1116-98-9 (tert-Butyl cyanoacetate) Hazard Symbols HarmfulXn
Synonyms

Aceticacid, cyano-, 1,1-dimethylethyl ester (9CI);Acetic acid, cyano-, tert-butylester (6CI,7CI,8CI);1,1-Dimethylethyl cyanoacetate;Cyanoacetic acidtert-butyl ester;Cyanoacetic acid tert-butyl ester;NSC 1072;tert-Butylcyanoacetate;

Article Data 23

tert-Butyl cyanoacetate Synthetic route

372-09-8

cyanoacetic acid

115-11-7

isobutene

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran at 10℃; under 12001.2 - 14251.4 Torr; for 0.133333h; Temperature; Solvent;98%
With boron trifluoride diethyl etherate In dichloromethane at 10℃; for 7h; Reagent/catalyst; Temperature; Solvent; Large scale;90%
With sulfuric acid; tert-butyl alcohol at -20℃;
372-09-8

cyanoacetic acid

75-65-0

tert-butyl alcohol

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;86%
With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 5h;84%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h;75%
107-59-5

tert-Butyl chloroacetate

151-50-8

potassium cyanide

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium iodide; tert-butyl alcohol
107-59-5

tert-Butyl chloroacetate

151-50-8

potassium cyanide

A

1116-98-9

cyanoacetic acid tert-butyl ester

B

106271-05-0

cyano-succinic acid di-tert-butyl ester

Conditions
ConditionsYield
With water; tert-butyl alcohol
5292-43-3

bromoacetic acid tert-butyl ester

151-50-8

potassium cyanide

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
With methanol
16130-58-8

cyanoacetic acid chloride

75-65-0

tert-butyl alcohol

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
With diethyl ether; N,N-dimethyl-aniline
5292-43-3

bromoacetic acid tert-butyl ester

13435-20-6

tetraethylammoniumcyanide

1116-98-9

cyanoacetic acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane

C23H25I2NO2

1116-98-9

cyanoacetic acid tert-butyl ester

C29H35I2NO4

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 50℃;100%
108-86-1

bromobenzene

1116-98-9

cyanoacetic acid tert-butyl ester

82102-37-2

9-methyl-9H-fluorene-9-carbonyl chloride

614-16-4

Benzoylacetonitrile

Conditions
ConditionsYield
Stage #1: bromobenzene; cyanoacetic acid tert-butyl ester; 9-methyl-9H-fluorene-9-carbonyl chloride With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With formic acid In 1,4-dioxane Reagent/catalyst; Inert atmosphere;
100%
1116-98-9

cyanoacetic acid tert-butyl ester

4175-77-3

2,4-dibromo-1,3-thiazole

tert-butyl 2-(4-bromothiazol-2-yl)-2-cyanoacetate

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 16h;100%

tert-Butyl cyanoacetate Specification

The Acetic acid, 2-cyano-,1,1-dimethylethyl ester, with the CAS registry number 1116-98-9, is also known as 1,1-Dimethylethyl cyanoacetate. It belongs to the product categories of C6 to C7; Carbonyl Compounds; Esters. Its EINECS number is 214-243-7. This chemical's molecular formula is C7H11NO2 and molecular weight is 141.17. What's more, its IUPAC name is methyl tert-butyl 2-cyanoacetate. It is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Its storage temperature is 2 - 8 °C. What's more, it should be protected from oxides and acids. It is harmful if swallowed. When using it, you should avoid contacting with skin and eyes. 

Physical properties of Acetic acid, 2-cyano-,1,1-dimethylethyl ester are: (1)ACD/LogP: 0.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.32; (4)ACD/LogD (pH 7.4): -1.73; (5)ACD/BCF (pH 5.5): 1; (6)ACD/KOC (pH 5.5): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 0; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 50.09 Å2; (11)Index of Refraction: 1.426; (12)Molar Refractivity: 36.13 cm3; (13)Molar Volume: 140.9 cm3; (14)Surface Tension: 33.3 dyne/cm; (15)Density: 1.001 g/cm3; (16)Flash Point: 79 °C; (17)Enthalpy of Vaporization: 43.08 kJ/mol; (18)Boiling Point: 194.6 °C at 760 mmHg; (19)Vapour Pressure: 0.438 mmHg at 25°C.

Uses of Acetic acid, 2-cyano-,1,1-dimethylethyl ester: it can be used to produce cyano-(1-methyl-pyrrolidin-2-ylidene)-acetic acid tert-butyl ester at the ambient temperature. It will need reagent NaOMe and solvent tetrahydrofuran with the reaction time of 1 hour. The yield is about 95%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C)OC(=O)CC#N
(2)InChI: InChI=1S/C7H11NO2/c1-7(2,3)10-6(9)4-5-8/h4H2,1-3H3
(3)InChIKey: BFNYNEMRWHFIMR-UHFFFAOYSA-N

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