Trimethyl phosphonoacetate
Basic information
- CAS
5927-18-4- Standard SMILES
COC(=O)CP(=O)(OC)OC- InChIKey
SIGOIUCRXKUEIG-UHFFFAOYSA-N- Molecular formula
- C5H11O5P
- Average molar mass
- 182.11 g/mol
- Monoisotopic mass
- 182.03441008
Overview
Trimethyl phosphonoacetate is a phosphonic ester.
Names & identifiers
- Preferred name
- Trimethyl phosphonoacetate
- IUPAC
- methyl 2-dimethoxyphosphorylacetate
- English name
- Trimethyl phosphonoacetate
- Molecular formula
- C5H11O5P
- Molecular weight
- 182.11
Names & synonyms
Trimethyl phosphonoacetate5927-18-4methyl 2-dimethoxyphosphorylacetateTrimethylacetyl phosphateAcetic acid, (dimethoxyphosphinyl)-, methyl esterDTXSID3064063RefChem:899798DTXCID5042588227-663-0Methyl 2-(dimethoxyphosphoryl)acetateTrimethyl phosphonacetateMFCD00008452
Show more names
TMPANSC 84262TriMethyl phosphonoacetatTRIMETHYL PHOPHONOACETATETrimethylphosphoroacetateRIMETHYL PHOSPHONOACETATE
C5H11O5PPhosphonoacetic Acid Trimethyl EsterDimethylphosphonoacetic Acid Methyl EsterMethyl DimethylphosphonoacetateMethyl (dimethoxyphosphoryl)acetate(Carboxymethyl)phosphonic acid trimethyl estermethyl-(dimethoxyphosphoryl)acetatEINECS 227-663-0
Database identifiers
- CAS
5927-18-4- PubChem CID
- 80029
- DTXSID
DTXSID3064063- ChEBI
CHEBI:195100- EC Number
- 227-663-0
- Nikkaji
- J227E
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 61.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 170
Physicochemical properties
- Melting point
- 242 °C · 242 °C
- Boiling point
- 118 °C0.85 · 118 °C0.85 mm Hg(lit.)
- Density
- 1.125 g/mL · 1.125 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.437(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- Liquid
- Specific Gravity
- 1.265 · approximate 1.265ｇ/ml (20℃)
- color
- Clear colorless to light yellow
- Water Solubility
- Slightly miscible with water.
- BRN
- 1865177 · 1865177
- InChI
- 1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
- InChIKey
- SIGOIUCRXKUEIG-UHFFFAOYSA-N
- SMILES
- COC(=O)CP(=O)(OC)OC
- LogP
- -0.68 · -0.680 (est)
- CAS DataBase Reference
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 87.5% (56 of 64) of all reports.
Warning
H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 28-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/10683
Acetic acid, (dimethoxyphosphinyl)-, methyl 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.
Hazard Classes and CategoriesSkin Irrit. 2 (12.5%)
Safety data
- F
- 9
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29310095
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationAcetic acid, 2-(dimethoxyphosphinyl)-, methyl ester: ACTIVE
Applications
UsesTrimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
156 records
Compound notes
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