Triethyl phosphonoacetate

HCID 13345CAS 867-13-0
Substructure searchFind similar structures

Basic information

Standard SMILES
CCOC(=O)CP(=O)(OCC)OCC
InChIKey
GGUBFICZYGKNTD-UHFFFAOYSA-N
Molecular formula
C8H17O5P
Average molar mass
224.19 g/mol
Monoisotopic mass
224.08136027

Names & identifiers

Preferred name
Triethyl phosphonoacetate
IUPAC
ethyl 2-diethoxyphosphorylacetate
English name
Triethyl phosphonoacetate
Molecular formula
C8H17O5P
Molecular weight
224.19

Names & synonyms

Triethyl phosphonoacetate867-13-0Ethyl (diethoxyphosphoryl)acetateEthyl (diethylphosphono)acetateTriethyl phosphonoethanoateAcetic acid, (diethoxyphosphinyl)-, ethyl esterDiethyl carbethoxymethylphosphonateDiethyl ethoxycarbonylmethanephosphonateDiethyl carboethoxymethylphosphonateEthyl diethoxyphosphoryl acetateTL 465ETHYL (DIETHOXYPHOSPHINYL)ACETATE
Show more names
ETHYL 2-(DIETHOXYPHOSPHORYL)ACETATEETHYL DIETHYLPHOSPHONOACETATETriethyl phosphonacetateTicagrelor Impurity 150Triethyl phosphonoacetatCarbethoxyMethyldiethyl PhosphonateDIETHYLPHOSPHONOACETIC ACID ETHYL ESTERDIETHYL ETHOXYCARBONYLMETHYLPHOSPHONATEtl465
Phosphonoacetic acid, triethyl esterAcetic acid, phosphono-, triethyl esterDiethyl phosphonoacetic acid, ethyl esterAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester(Ethoxycarbonylmethyl)diethoxyphospshine oxideDTXSID4041573Acetic acid, diethylphosphono-, ethyl esterNSC-13898

Database identifiers

CAS
867-13-0
PubChem CID
13345
DTXSID
DTXSID4041573
ChEMBL
CHEMBL3185304
UNII
022826171T
EC Number
212-757-6
Nikkaji
J54.207E

Properties

Computed structural properties

XLogP
0.5
Topological polar surface area
61.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
8
Heavy atoms
14

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organophosphates, Other
Food Contact Substances · 2 items

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Physical DescriptionClear light yellow liquid; [Acros Organics MSDS]
Collision Cross Section143.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4041573]

Physicochemical properties

Melting point
-24 °C · -24°C
Boiling point
142 · 142-145 °C9 mm Hg(lit.)
Density
1.13 g/mL · 1.13 g/mL at 25 °C(lit.)
vapor pressure
0.61 Pa · 0.61Pa at 25℃
refractive index
20 · n20/D 1.431(lit.)
Flash point
165 °C · 165°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (22.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: Acetic acid, (diethoxyphosphinyl)-, ethyl ester

Regulation (EC) No 1935/2004 (amended)

Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11013

Acetic acid, (diethoxyphosphinyl)-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryOral lethal-dose (rat) > 500 mg/kg; [RTECS] An irritant that may cause serious eye injury; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (22.9%)

Toxicology

Toxicity DataLCLo (mouse) = 1,180 mg/m3/10min

Safety data

PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
3
tsca
TSCA listed
rtecs
AG9800000
ridadr
UN 3082 9/PG 3
hs_code
29310095

Chemistry & industry

Uses & manufacturing

UsesUsed to make large scale and fine chemicals, active pharmaceutical ingredients or fragrances, and to polymerize bottle grade PET; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationAcetic acid, 2-(diethoxyphosphinyl)-, ethyl ester: ACTIVE
Applications · 3 items

DescriptionTriethyl 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].

UsesTriethyl phosphonoacetate is used for Horner-Emmons modification.

UsesTriethyl phosphonoacetate serves as a reactant used in Horner-Wadsworth-Emmons reactions, Tsuji-Trost type reactions, Intramolecular Heck-type cyclization and isomerizations and Intramolecular aryne-ene reactions. In Horner-Wadsworth-Emmons reaction, it is utilized as a reagent to prepare chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东德信精细化工有限公司18553366272

Related reactions

830 records
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Linked notes

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