Dimethyl malonate

HCID 7943CAS 108-59-8
Substructure searchFind similar structures

Basic information

Standard SMILES
COC(=O)CC(=O)OC
InChIKey
BEPAFCGSDWSTEL-UHFFFAOYSA-N
Molecular formula
C5H8O4
Average molar mass
132.11 g/mol
Monoisotopic mass
132.04225874

Overview

dimethyl malonate has been reported in Astragalus mongholicus, Astragalus membranaceus, and Myrtus communis with data available.

Names & identifiers

Preferred name
Dimethyl malonate
IUPAC
dimethyl propanedioate
English name
Dimethyl malonate
Molecular formula
C5H8O4
Molecular weight
132.11

Names & synonyms

Dimethyl malonate108-59-8Dimethyl propanedioateMethyl malonateMALONIC ACID, DIMETHYL ESTERDTXSID4029145EM8Y79998CDTXCID309145RefChem:134253203-597-8Malonic Acid Dimethyl EsterPropanedioic acid, dimethyl ester
Show more names
DMMdimthyl malonateDIMETHYL MALONATdimethyl1,3-propanedioateMINA-009Malonic acid dDimethyl malote
1,3-dimethyl propanedioateC5H8O4MFCD00008460Malonic acid-dimethyl esterDimethyl 1,3-propanedioateCAS-108-59-8CCRIS 8981propanedioic acid dimethyl ester

Database identifiers

CAS
108-59-8
PubChem CID
7943
DTXSID
DTXSID4029145
ChEMBL
CHEMBL1986332
UNII
EM8Y79998C
EC Number
203-597-8
Nikkaji
J1.499K

Properties

Computed structural properties

XLogP
0
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Esters, Other
SpringerMaterials PropertiesBoiling point
LogP-0.05
Flavoring AgentsEU Flavoring substances
Vapor Pressure14.7 [mmHg]
Physical Description · 2 items

Liquid

Liquid; [Merck Index] Colorless liquid with an ester-like odor; [OECD SIDS: Malonic Acid Diesters - 2005]

Physicochemical properties

Melting point
-62 °C · -62 °C (lit.)
Boiling point
180 · 180-181 °C (lit.)
Density
1.156 g/mL · 1.156 g/mL at 25 °C (lit.)
vapor density
1 · >1 (vs air)
vapor pressure
0.15 hPa · 0.15 hPa (20 °C)
refractive index
20 · n20/D 1.413(lit.)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 86.3% (1530 of 1773) of all reports.

Warning

H319 (13.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 1773 reports by companies from 16 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 5 items

Chemical: Propanedioic acid, dimethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Propanedioic acid, 1,3-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedioic acid, 1,3-dimethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 04-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20020

Dimethyl malonate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazards Summary · 1 item

Causes no skin irritation and mild to moderate eye irritation in rabbits; No adverse effects observed in oral or dermal lethal-dose studies of rats (LD50s > 2,000 mg/kg); Reversible hepatocellular hypertrophy (considered indicative of liver metabolism rather than systemic toxicity) observed in an oral repeated-dose study of rats at the highest tested dose (1,000 mg/kg/day); No evidence of reproductive toxicity, developmental toxicity, or mutagenicity; [OECD SIDS: Malonic Acid Diesters - 2005] May cause irritation; [Alfa Aesar MSDS]

Hazard Classes and CategoriesEye Irrit. 2 (13.6%)

Safety data

wgk
1
tsca
TSCA listed
rtecs
OO0950000
ridadr
NA1993
hs_code
29171910
Toxicity
LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Chemistry & industry

Uses & manufacturing

UsesNaturally occurring as a volatile in fruits such as pineapples, bananas, and blackberries; Used as an intermediate for agrochemicals, pharmaceuticals, industrial chemicals, and other compounds; [OECD SIDS: Malonic Acid Diesters - 2005]
U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Propanedioic acid, 1,3-dimethyl ester: ACTIVE

Applications · 4 items

DescriptionDimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.

UsesIt is used in fragrances and some artificial flavorings .

UsesDimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.

General DescriptionDimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines.

Upstream & downstream products

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]
济南宏嘉化工有限公司15253128188; 15253128188

Related reactions

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Linked notes

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