CAS 28868-76-0 Dimethyl chloromalonate (HCID 120070)

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Basic information

CAS: 28868-76-0
Standard SMILES: COC(=O)C(Cl)C(=O)OC
InChIKey: LNBQBURECUEBKZ-UHFFFAOYSA-N
Molecular formula: C5H7ClO4
Average molar mass: 166.56 g/mol
Monoisotopic mass: 166.00328638

Names & identifiers

Preferred name: Dimethyl chloromalonate
IUPAC: dimethyl 2-chloropropanedioate
English name: Dimethyl chloromalonate
Molecular formula: C5H7ClO4
Molecular weight: 166.56

Names & synonyms

Dimethyl chloromalonate28868-76-0Dimethyl 2-chloromalonateDTXSID6049018QH3S4XL5PIPropanedioic acid, chloro-, dimethyl esterEINECS 249-275-0DTXCID1028944Propanedioic acid, 2-chloro-, 1,3-dimethyl esterDIMETHYL .ALPHA.-CHLOROMALONATECHLOROPROPANEDIOIC ACID DIMETHYL ESTERMALONIC ACID, CHLORO-, DIMETHYL ESTER

Show more names

CL-DMMAURORA KA-6079Dimethyl chloromaloteChloro-Methyl MalonateEthylsuccinyl monochlorideChlorotwoMethylMalonic aciDiMethyl chloroMalonate 94%ChlorotwoMethylMalonic acidimethyl2-chloropropanedioate

RefChem:588257DIMETHYL ALPHA-CHLOROMALONATE249-275-0dimethyl 2-chloropropanedioate1,3-dimethyl 2-chloropropanedioateMFCD00042837dimethyl chloropropanedioateNCGC00249607-01

Database identifiers

CAS: 28868-76-0
PubChem CID: 120070
DTXSID: DTXSID6049018
ChEMBL: CHEMBL3185914
UNII: QH3S4XL5PI
EC Number: 249-275-0
Nikkaji: J286.469J

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 52.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 10
Formal charge: 0
Complexity: 129

Physicochemical properties

Boiling point: 105 · 105-106 °C/19 mmHg (lit.)
Density: 1.305 g/mL · 1.305 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.437(lit.)
Flash point: 224 °F · 224 °F
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: clear liquid
pka: 9.02 · 9.02±0.46(Predicted)
color: Colorless to Light yellow
BRN: 1768415 · 1768415
InChI: InChI=1S/C5H7ClO4/c1-9-4(7)3(6)5(8)10-2/h3H,1-2H3
InChIKey: LNBQBURECUEBKZ-UHFFFAOYSA-N
SMILES: C(OC)(=O)C(Cl)C(OC)=O
CAS DataBase Reference: 28868 · 28868-76-0(CAS DataBase Reference)
FDA UNII: 3 S4XL5PI · QH3S4XL5PI
UNSPSC Code: 12352100 · 12352100
NACRES

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (97.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1B (97.7%)

Safety data

F: 21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 3265 8/PG 2
hs_code: 2917198090
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
Hazard statements: H314
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications

Chemistry & industry

Applications · 2 items

UsesDimethyl chloromalonate is suitable for use in the synthesis of 4,5,6-trichloropyrimidine. It may be used in the stereoselective synthesis of highly functionalized nitrocyclopropanes. It may be used in one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.

General DescriptionDimethyl chloromalonate (dimethyl 2-chloromalonate) is a dialkyl 2-substituted malonate. Carbanions of dimethyl chloromalonate are reported to react with naphthoquinone derivatives, via vicarious nucleophilic substitution or oxidative nucleophilic substitution of hydrogen processes. Dimethyl chloromalonate is reported to react with hydroquinone and monosubstituted hydroquinones to afford 2-oxido-benzo[b]furan derivatives. Synthesis of dimethyl 2-chloromalonate, via chlorination of dimethyl malonate has been reported.