CAS 5436-21-5 4,4-Dimethoxy-2-butanone (HCID 228548)

Overview

4,4-Dimethoxy-2-butanone is a ketone.

Names & identifiers

Preferred name: 4,4-Dimethoxy-2-butanone
IUPAC: 4,4-dimethoxybutan-2-one
English name: Acetylacetaldehyde dimethyl acetal
Molecular formula: C6H12O3
Molecular weight: 132.16

Names & synonyms

4,4-dimethoxybutan-2-one4,4-Dimethoxy-2-butanoneAcetylacetaldehyde dimethyl acetal2-Butanone, 4,4-dimethoxy-1,1-Dimethoxy-3-butanoneAcetoacetaldehyde dimethyl acetal3-Oxobutyraldehyde dimethyl acetal4,4-DimethoxybutanoneFormylacetone dimethyl acetalAcetylacetaldehyddimethylacetal3-Oxobutanal dimethyl acetal3-Ketobutyraldehyde dimethylacetal

Show more names

KBAAADMA4,4-dimethoxybutanon4,4-Dimethoxy-2-butanone (DMB)3-OXOBUTYRALDEHYDE DIMETHYLACETALFADMA

Acetoacetaldehyde, 1-(dimethyl acetal)FEMA No. 3381beta-Oxobutyraldehyde dimethyl acetalNSC 21538NSC 59721Acetoacetaldehyde 1-(dimethyl acetal)UNII-0IZ188B2ZAEINECS 226-605-1

Database identifiers

CAS: 5436-21-5
PubChem CID: 228548
DTXSID: DTXSID8052196
ChEBI: CHEBI:173539
UNII: 0IZ188B2ZA
EC Number: 226-605-1
Nikkaji: J150.136D

Properties

Computed structural properties

XLogP: -0.3
Topological polar surface area: 35.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 9
Formal charge: 0
Complexity: 86.3

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds

SpringerMaterials PropertiesChemical shift

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density0.993-0.998

Flavoring AgentsEU Flavoring substances

Solubility · 2 items

slightly

(in ethanol)

Physicochemical properties

Melting point: -82 °C · -82 °C
Boiling point: 70 · 70-73 °C/20 mmHg (lit.)
Density: 0.996 g/mL · 0.996 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.414(lit.)
FEMA: 3381 · 3381 | 3-OXOBUTANAL DIMETHYL ACETAL
FLAVIS Number: 6.038 · 06.038 | 4,4-Dimethoxybutan-2-one
Flash point: 121 °F · 121 °F
storage temp.: Inert atmosphere,Room Temperature
solubility: soluble in Chloroform, Ethyl Acetate
form: Liquid
color: Clear colorless to yellow
Odor: 0.1 % · at 0.10 % in dipropylene glycol. ethereal musty nutty alcoholic bitter
Odor Type: ethereal
Water Solubility: decomposes
JECFA Number: 593 · 593
BRN: 1702372 · 1702372
InChI: 1S/C6H12O3/c1-5(7)4-6(8-2)9-3/h6H,4H2,1-3H3
InChIKey: PJCCSZUMZMCWSX-UHFFFAOYSA-N
SMILES: COC(CC(C)=O)OC
LogP: 0.33 · 0.33
CAS DataBase Reference: 5436 · 5436-21-5(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): 3 · 3-OXOBUTANAL, DIMETHYL ACETAL
EWG's Food Scores: 1 · 1
FDA UNII: 0 IZ188B2ZA · 0IZ188B2ZA
NIST Chemistry Reference: 2 · 2-Butanone, 4,4-dimethoxy-(5436-21-5)
EPA Substance Registry System: 2 · 2-Butanone, 4,4-dimethoxy- (5436-21-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Warning
Hazard statements: 226 · H226
Precautionary statements: 210 · P210-P233-P240-P241-P242-P243
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: F
Risk Statements: 10 · 10
Safety Statements: 16 · 16
RIDADR: 1989 · UN 1989 3/PG 3
WGK Germany: 2 · 2
RTECS: 7592500 · EL7592500
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29145000 · 29145000
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 · Flam. Liq. 3
REACH Registrations: Inactive
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 5.6% (89 of 1598) of reports.

Warning

H226 (94.4%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1598 reports by companies from 7 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: 2-Butanone, 4,4-dimethoxy-

2-Butanone, 4,4-dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, 4,4-dimethoxy- 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: 25-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27682

2-Butanone, 4,4-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses somnolence and convulsions in oral lethal-dose studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS] See 2-Butanone.

Hazard Classes and CategoriesFlam. Liq. 3 (94.4%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 2
tsca: TSCA listed
rtecs: EL7592500
ridadr: UN 1989 3/PG 3
hs_code: 29145000
risk_code: 10
Signal word: Warning
Symbol(GHS): GHS02
hazard_code: F
safety_code: 16
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations: Inactive
Hazard Classifications: Flam. Liq. 3
Precautionary statements: P210-P233-P240-P241-P242-P243

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUsed as a flavoring agent; [FDA]

U.S. Production2020: 167,993 lb

Use Classification · 3 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information2-Butanone, 4,4-dimethoxy-: ACTIVE

Applications · 3 items

UsesAcetaldehyde dimethyl acetal is used as a flavoring agent. It is also used in the preparation of (R)-4,4-dimethoxy-2-butanol, pyrazoles and pyrimidines. Further, it is used in the preparation of N,N-diethyl-[2-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]-pyrimidin-3-yl]acetamide and acetoacetaldehyde.

Uses4,4-Dimethoxy-2-butanone (β-ketobutyracetal) may be used in the preparation of:(R)-4,4-dimethoxy-2-butanolpyrazoles and pyrimidines[7,16-dihydro- 6,15( 17)-dimetbyldibenzo[b,i]-[1,4,8,11]tetrilazacyclotetradecinato-N5,N9,N14,N18]nickel{II)

General Description4,4-Dimethoxy-2-butanone (Acetylacetaldehyde dimethylacetal) is a ketone.

Upstream & downstream products

Upstream raw materials

Downstream products

Methyl 3-methyl-2-furoate 1-Methoxy-3-trimethylsiloxy-1,3-butadiene 2-Methanesulfonyl-4-methyl-pyrimidine 5-Methyl-4-isoxazolesulfonyl chloride Ethyl 5-methyl-1H-pyrrole-2-carboxylate 4-Methoxy-3-buten-2-one 4-Methyl-pyrimidine-2-sulfonyl fluoride 3-Methyl-2-furoic acid 3-Methyl-1-phenylpyrazole 4-Methyl-2-(methylsulfanyl)pyrimidine 4 4-Dimethoxy-2-methyl-2-butanol 97 2-Fluoro-6-methylnaphthalene

Suppliers100 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]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: 4,4-Dimethoxy-2-butanone is a ketone.

Related reactions

48 records

New reaction record

HRID 49185As reactantuspto-grants-2004_03

HRID 160865As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)

HRID 224457As reactantuspto-grants-1980_11

HRID 236281As reactantuspto-grants-1987_02

HRID 397894As reactantuspto-grants-2003_08

HRID 433588As reactantuspto-grants-2003_12

HRID 477218As reactantuspto-grants-1989_12

HRID 547979As reactantuspto-grants-2011_05

Compound notes

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Basic information