Triethyl phosphonoacetate , 98% , 867-13-0

Synonym(s):
(Diethoxyphosphinyl)acetic acid ethyl ester;Diethyl ethoxycarbonylmethylphosphonate;NSC 13898;NSC 16128;Triethyl carboxymethylphosphonate

CAS NO.：867-13-0

Empirical Formula: C8H17O5P

Molecular Weight: 224.19

MDL number: MFCD00009177

EINECS: 212-757-6

PRODUCT Properties

• Melting point: -24°C
• Boiling point: 142-145 °C9 mm Hg(lit.)
• Density: 1.13 g/mL at 25 °C(lit.)
• vapor pressure: 0.61Pa at 25℃
• refractive index: n20/D 1.431(lit.)
• Flash point: 165°C
• storage temp.: Keep in dark place,Sealed in dry,Room Temperature
• solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• form: Liquid
• color: Clear
• Specific Gravity: 1.130
• Water Solubility: Slightly miscible with water.
• BRN: 1343714
• InChIKey: GGUBFICZYGKNTD-UHFFFAOYSA-N
• LogP: 1.13 at 30℃
• CAS DataBase Reference: 867-13-0(CAS DataBase Reference)
• EPA Substance Registry System: Acetic acid, (diethoxyphosphinyl)-, ethyl ester (867-13-0)

Description and Uses

Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification. This compound can be added dropwise to sodium methoxide solution to prepare a phosphonate anion. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl, the resulting alkene formed is usually the E alkene and is generated with excellent regioselectivity. It can synthesize β-Keto Phosphonates via an acylation reaction of triethyl phosphonoacetate with carboxylic acid chlorides in the presence of magnesium chloride-triethylamine followed by decarbethoxylation. Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates, which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates[1-2].

Triethyl phosphonoacetate is used for Horner-Emmons modification.

Safety

• Symbol(GHS): GHS07,GHS09
• Signal word: Warning
• Hazard statements: H319-H411
• Precautionary statements: P264-P273-P280-P305+P351+P338-P337+P313-P391
• Hazard Codes: N,Xi,Xn
• Risk Statements: 51/53-36/37/38
• Safety Statements: 61-37/39-26-36
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• RTECS: AG9800000
• Hazard Note: Harmful
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• HS Code: 29310095