3-Butene-1,2-diol (HCID 10338)

Overview

major industrial chemical; structure given in first source

Names & identifiers

Preferred name: 3-Butene-1,2-diol
IUPAC: but-3-ene-1,2-diol
English name: 3-Butene-1,2-diol
Molecular formula: C4H8O2
Molecular weight: 88.11

Names & synonyms

3-BUTENE-1,2-DIOL497-06-33,4-Dihydroxy-1-butene1,2-Dihydroxy-3-butenePP8001HM3TRefChem:499468207-835-1but-3-ene-1,2-diol1-Butene-3,4-diolMFCD0023941086161-40-23,4-Dihydroxy-1-butene; Erythrol;

Show more names

ErythrolEPB(TM) DIOL3-buten-1,2-diolR,S-3-BUTENE-1,2-DIOL(±)-3-Butene-1,2-Diol

EINECS 207-835-1Butene glycolAI3-07552CCRIS 9376( inverted exclamation markA)-3-Butene-1,2-diolUNII-PP8001HM3TSCHEMBL93405SCHEMBL4634738

Database identifiers

CAS: 497-06-3、86161-40-2
PubChem CID: 10338
DTXSID: DTXSID60870564
UNII: PP8001HM3T
EC Number: 207-835-1
Nikkaji: J25.059G

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 40.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 6
Formal charge: 0
Complexity: 42.8

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Other Monomers

Vapor Pressure0.24 [mmHg]

Physical DescriptionClear colorless liquid with a mild odor of alcohol; [Acros Organics MSDS]

Physicochemical properties

Melting point: 15.1 °C · 15.1°C (estimate)
Boiling point: 195 °C/733 · 195 °C/733 mmHg (lit.)
Density: 1.047 g/mL · 1.047 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.462
Flash point: 222 °F · 222 °F
storage temp.: -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Oil
pka: 13.68 · 13.68±0.20(Predicted)
Specific Gravity: 1.047 · 1.047
color: Clear Colorless
optical activity: 1.7875 ° · 1.7875°(C=1g/100ml DCM)
BRN: 1633578 · 1633578
Henry's Law Constant: 7.8 · 7.8×102 mol/(m3Pa) at 25℃, Wang et al. (2017)
InChI: InChI=1S/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2
InChIKey: ITMIAZBRRZANGB-UHFFFAOYSA-N
SMILES: C(O)C(O)C=C
FDA UNII: 8001 HM3T · PP8001HM3T
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332
Precautionary statements: 261 · P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 36 · 36/37/38-20/21/22
Safety Statements: 36 · 36
WGK Germany: 3 · 3
F: 10 · 10
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards Summary · 1 item

Causes changes in urine in 4-week inhalation studies of rats and mice; Causes other liver changes and hypoglycemia in acute intraperitoneal studies of mice; Intraperitoneal LD50 (rat) = 250 mg/kg; [RTECS] A reactive monomer that gradually polymerizes at room temperature; An irritant; [Acros Organics MSDS] See 1,4-Dihydroxy-2-butene and 3-Buten-2-ol.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

F: 10
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
risk_code: 36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 36
Storage Class: 10 - Combustible liquids
Hazard statements: H302+H312+H332
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Precautionary statements: P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312

Chemistry & industry

Uses & manufacturing

UsesMajor industrial chemical. [ChemIDplus]

Applications · 3 items

UsesDecomposition product of Erythritol.

Uses3,4-Dihydroxy-1-butene can be used:As a reactant to synthesize cyclic organic carbonates by continuous flow procedure.To prepare substituted oxazolidinone ligands used to target medicinally relevant RNAs.

General Description3,4-Dihydroxy-1-butene, also known as 3-butene-1,2-diol (BDdiol), is a metabolite of 1,3-butadiene. It forms the precursor for synthesizing different chiral building blocks. BDdiol can undergo oxidation to form hydroxymethylvinyl ketone (HMVK). 1,2-epoxy-3-butene (EB) on hydrolysis in the presence of epoxide hydrolases (EH) forms BDdiol.