2-Cyano-3-methyl-but-2-enoic acid ethyl ester

HCID 136573

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Basic information

CAS: 759-58-0
Standard SMILES: CCOC(=O)C(C#N)=C(C)C
InChIKey: PZMDAADKKAXROL-UHFFFAOYSA-N
Molecular formula: C8H11NO2
Average molar mass: 153.18 g/mol
Monoisotopic mass: 153.07897859

Names & identifiers

Preferred name: 2-Cyano-3-methyl-but-2-enoic acid ethyl ester
IUPAC: ethyl 2-cyano-3-methylbut-2-enoate
English name: Ethyl 2-cyano-3-methylcrotonate
Molecular formula: C8H11NO2
Molecular weight: 153.18

Names & synonyms

2-Cyano-3-methyl-but-2-enoic acid ethyl esterRefChem:470632625-950-9759-58-0ethyl 2-cyano-3-methylbut-2-enoateEthyl 2-cyano-3-methylcrotonateEthyl 2-cyano-3-methyl-2-butenoate2-Butenoic acid, 2-cyano-3-methyl-, ethyl esterEthyl isopropylidene(cyano)acetateMFCD00009135Crotonic acid, 2-cyano-3-methyl-, ethyl esterethyl isopropylidenecyanoacetate

Show more names

Ethyl 2-cyano-3-methylbutanoateTIMTEC-BB SBB007715Ethyl 2-cyano-3-methyl-2-butanoateEthyl 2-cyano-3-methyl-2-butenoate,98%Ethyl 2-cyano-3-methyl-2-butenoate,97%2-cyano-3-methylcrotonic acid ethyl ester

NSC-1074NSC-11260NSC-127868UYK6XD7QF42-cyano-3-methyl-2-butenoic acid ethyl esterethylisopropylidenecyanoacetateSCHEMBL1261327DTXSID20226821

Database identifiers

CAS: 759-58-0
PubChem CID: 136573
DTXSID: DTXSID20226821
UNII: UYK6XD7QF4
EC Number: 625-950-9
Nikkaji: J100.077B

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 50.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 228

Physicochemical properties

Melting point: 20 ℃ · ca 20℃
Boiling point: 98 · 98-99 °C/1 mmHg (lit.)
Density: 1.014 g/mL · 1.014 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.464(lit.)
Flash point: 224 °F · 224 °F
BRN: 507839 · 507839
InChI: 1S/C8H11NO2/c1-4-11-8(10)7(5-9)6(2)3/h4H2,1-3H3
InChIKey: PZMDAADKKAXROL-UHFFFAOYSA-N
SMILES: CCOC(=O)\C(C#N)=C(\C)C
UNSPSC Code: 12352100 · 12352100
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 26 · 26-37/39
RIDADR: 3276 · 3276
WGK Germany: 3 · 3
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29269095 · 29269095
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: 3276
hs_code: 29269095
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-37/39
hazard_class: 6.1
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H302+H312+H332-H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338

Chemistry & industry

Applications

UsesEthyl 2-cyano-3-methyl-2-butenoate, a highly activated acceptor, undergoes the phospha-Michael reaction upon trituration of the reagents at room temperature.

General DescriptionEthyl 2-cyano-3-methyl-2-butenoate, a highly activated acceptor, undergoes the phospha-Michael reaction upon trituration of the reagents at room temperature.