Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester (HCID 17453)

Names & identifiers

Preferred name: Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester
IUPAC: methyl 2-(triphenyl-λ5-phosphanylidene)acetate
English name: Methyl (triphenylphosphoranylidene)acetate
Molecular formula: C21H19O2P
Molecular weight: 334.35

Names & synonyms

2605-67-6Methyl (triphenylphosphoranylidene)acetate(Carbomethoxymethylene)triphenylphosphoraneAcetic acid, (triphenylphosphoranylidene)-, methyl ester(Triphenylphosphoranylidene)acetic acid methyl esterMethyl triphenylphosphoranylideneacetateTriphenyl(carbomethoxymethylene)phosphoraneAcetic acid, 2-(triphenylphosphoranylidene)-, methyl esterEINECS 220-018-4((Methoxycarbonyl)methylene)triphenylphosphorane[(Methoxycarbonyl)methylene]triphenylphosphoraneNSC 117573

Show more names

(METHOXYCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANEmethyl 2-(triphenyl-λ-phosphanylidene)acetateCMETPPAURORA KA-874idene)acetatemethyl 2-(triphenyl-Aceticacid,(triphenylphosphoranylideneMethyl (triphenylphosphoranylidene)acet

NSC 407395DTXSID6062549RefChem:552122DTXCID5037440220-018-4InChI=1/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1HMethyl 2-(triphenylphosphoranylidene)acetateCARBOMETHOXYMETHYLENE TRIPHENYLPHOSPHORANE

Database identifiers

CAS: 2605-67-6
PubChem CID: 17453
DTXSID: DTXSID6062549
ChEMBL: CHEMBL1715161
UNII: D9MZ753Q8K
EC Number: 220-018-4
Nikkaji: J24.865G

Properties

Computed structural properties

XLogP: 4
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 5
Heavy atoms: 24
Formal charge: 0
Complexity: 400

Experimental & physicochemical properties

SpringerMaterials PropertiesCrystal structure

Physicochemical properties

Melting point: 168 · 168-172 °C (lit.)
Boiling point: 165 · 165~170℃
Density: 1.17 · 1.17±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Acetonitrile (Slightly), Chloroform (Slightly)
form: Powder
color: White to off-white
Water Solubility: insoluble
Sensitive: Air Sensitive
BRN: 618430 · 618430
InChI: InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3
InChIKey: NTNUDYROPUKXNA-UHFFFAOYSA-N
SMILES: C(OC)(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
CAS DataBase Reference: 2605 · 2605-67-6(CAS DataBase Reference)
FDA UNII: 9 MZ753Q8K · D9MZ753Q8K
EPA Substance Registry System: Acetic acid, (triphenylphosphoranylidene)-, methyl ester (2605-67-6)
UNSPSC Code: 12352108 · 12352108
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: T,Xi
Risk Statements: 36 · 36/37/38-25
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29319090 · 29319090
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.

Danger

H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, 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 4 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Acetic acid, (triphenylphosphoranylidene)-, methyl ester

Status: Active Update: 21-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28364

Hazard Classes and CategoriesAcute Tox. 3 (50%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
hs_code: 29319090
risk_code: 36/37/38-25
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: T,Xi
hazard_note: Irritant
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationAcetic acid, 2-(triphenylphosphoranylidene)-, methyl ester: ACTIVE

Applications · 3 items

Uses(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene.

UsesWittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. Also used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.

Uses(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine. It is used in the preparation of (triphenylphosphoranylidene)-ketene. The Wittig reaction we performed in class involved the reaction of 2-nitrobenzaldehyde (1) with methyl (triphenylphosphoranylidene) acetate (2) to produce methyl (2E)-3-(2-nitrophenyl) acrylate (3) with a triphenylphosphine oxide (4) side product, and took place in a silica gel matrix to ensure even product dispersion for chromatography.