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Butan-1,2-diol

1,2-Butanediol

HCID 11429
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Grundinformationen

CAS
584-03-2
Standard-SMILES
CCC(O)CO
InChIKey
BMRWNKZVCUKKSR-UHFFFAOYSA-N
Summenformel
C4H10O2
Durchschnittliche Molmasse
90,12 g/mol
Monoisotopische Masse
90,06807956

Überblick

Butane-1,2-diol is a butanediol in which the two hydroxy groups are located at positions 1 and 2. It has a role as a metabolite. It is a glycol and a butanediol.

Namen und Bezeichner

Bevorzugter Name
1,2-Butanediol
IUPAC
butane-1,2-diol
Lokaler Name
Butan-1,2-diol
Englischer Name
1,2-BUTANEDIOL
Summenformel
C4H10O2
Molmasse
90.12

Namen und Synonyme

1,2-BUTANEDIOL584-03-2butane-1,2-diol1,2-Butylene glycol1,2-Dihydroxybutanealpha-Butylene glycolalpha-ButyleneglycolDTXSID6040375RUN0H01QEUNSC-24242DTXCID4020375CHEBI:52682
Weitere Namen anzeigen
1,2-Butanediol,98%NSC 24242BDO Liquid1,2-Butanediol >BDO 1,2-BUTANEDIOL
Massage OilRefChem:934958209-527-226171-83-5Butanediol, 1,2-1,2-(Dihydroxy)butane1,2-ButandiolDL-1,2-Butanediol

Datenbank-Bezeichner

CAS
584-03-2
PubChem CID
11429
DTXSID
DTXSID6040375
ChEBI
CHEBI:52682
UNII
RUN0H01QEU
EC Number
209-527-2
Nikkaji
J46.396E

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,2
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
6
Formalladung
0
Komplexität
28,7

Experimentelle und physikochemische Eigenschaften

PolymersOther Classes -> Alcohols and Polyols, Other
CosmeticsCosmetic ingredients (1,2-Butanediol) -> CIR (Cosmetic Ingredient Review)
LogP-0.34 (20 °C)
Density · 2 Einträge

1.0023 @ 20 °C

Relative density (water = 1): 1.01

Viscosity · 2 Einträge

Dynamic viscosity @ 20 °C is 7.3 mPa.s

7.3 mm²/s at 20 °C

Color/FormCLEAR VISCOUS LIQUID
Solubility · 3 Einträge

SPECIFIC OPTICAL ROTATION: -7.4 DEG AT 22 °C/D (ALCOHOL, 4%); SOL IN WATER, ALCOHOL & ACETONE /L-FORM/

Miscible with water in all proportions, readily soluble in alcohols, slightly soluble in ethers and esters, and insoluble in hydrocarbons.

Solubility in water: miscible

Flash Point · 3 Einträge

90 °C

40 °C (104 °F) (CLOSED CUP)

93 °C c.c.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 25.3% (39 of 154) of reports.

Warning

H319 (74.7%): 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 154 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1,2-Butanediol

1,2-Butanediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Butanediol 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: 09-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23064

1,2-Butanediol: 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.

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Fire HazardsCombustible. Above 93 °C explosive vapour/air mixtures may be formed.
Fire PotentialModerate, when exposed to heat or flame.
Hazards SummaryAn eye irritant; High-level exposure could cause CNS depression and kidney injury; [ICSC] May cause irritation; [MSDSonline]
UN Classification

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

... 1.0 g/kg of 1,2 butanediol /given/ intravenously during a 2-min period to rabbits ... was metabolized slowly, as shown by the fact that the blood level fell slowly and that there was only slow excretion via the urine. That which was excreted in the urine was found either as the glucuronide or unchanged. Tissue analysis showed no accumulation of 1,2-butanediol.

... Glucuronides or other metabolites /were not found/ in the urine of rabbits given 1,2-butanediol orally.

Absorption, Distribution and Excretion... EVEN WHEN EXPOSURES WERE PROLONGED AND REPEATED ... IT WAS NOT ABSORBED THROUGH THE SKIN /OF RABBITS/ IN TOXIC AMT.

Verwendung und Herstellung

Uses · 5 Einträge

CIR ingredient: 1,2-Butanediol

Used as an intermediate in polyester resins; as a solvent; [HSDB] Used as a solvent in pesticides and inkjet inks and in the preparation of polyurethanes; [CHEMINFO]

Farming (Pesticides) [Category: Industry]

IN INDUST AS INTERMEDIATE IN POLYESTER RESINS

Solvent and intermediate

U.S. Production · 3 Einträge

2023: 250,000 - <550,000 lb

(1977) MORE THAN 4.5X10+6 G (INCL 1,3-ISOMER)

(1979) MORE THAN 4.5X10+6 G (INCL 1,3-ISOMER)

Consumer UsesSolvent
Methods of Manufacturing1,2-BUTANEDIOL IS A RELATIVELY NEW PRODUCT & IS PRODUCED COMMERCIALLY BY HYDRATION OF CORRESPONDING 1,2-BUTYLENE OXIDE IN MANNER SIMILAR TO THAT DESCRIBED FOR OTHER SIMPLE GLYCOLS.
Use Classification · 2 Einträge

EPA Safer Chemical Functional Use Classes -> Solvents

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Zugehörige Reaktionen

37
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 132707
HRID 132707als Eduktuspto-grants-2008_06
Reaktionsgleichung von HRID 188103
HRID 188103als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 204820
HRID 204820als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 223316
HRID 223316als Eduktuspto-grants-1982_10
Reaktionsgleichung von HRID 263048
HRID 263048als Eduktuspto-grants-1979_05
Reaktionsgleichung von HRID 274827
HRID 274827als Eduktuspto-grants-1995_02
Reaktionsgleichung von HRID 274828
HRID 274828als Eduktuspto-grants-1995_02
Reaktionsgleichung von HRID 287581
HRID 287581als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
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Boiling Point · 2 Einträge

195-196.9 °C

194 °C

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 2 Einträge

-50 °C

-114 °C

Vapor Density · 2 Einträge

3.1 (AIR= 1)

Relative vapor density (air = 1): 3.1

Physikochemische Eigenschaften

Schmelzpunkt
-50 °C · -50 °C
Siedepunkt
191 · 191-192 °C/747 mmHg (lit.)
Dichte
1.006 g/mL · 1.006 g/mL at 25 °C (lit.)
Dampfdruck
10 · 10-2130Pa at 20℃
Brechungsindex
20 · n20/D 1.438(lit.)
Flammpunkt
200 °F · 200 °F
storage temp.
2 · Storage temp. 2-8°C
Aggregatzustand
clear liquid
pka
14.49 · 14.49±0.20(Predicted)
Farbe
Colorless to Light yellow
Wasserlöslichkeit
100 · 100-1000g/L at 25℃
BRN
969169 · 969169
Henry's Law Constant
2.1 · 2.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
Kosmetik-Inhaltsstoffe Funktionen
SOLVENTSKIN CONDITIONINGHUMECTANTVISCOSITY CONTROLLING
InChI
1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
InChIKey
BMRWNKZVCUKKSR-UHFFFAOYSA-N
SMILES
CCC(O)CO
LogP
-0.34 · -0.34-0.3 at 25℃
CAS Datenbank
584 · 584-03-2(CAS DataBase Reference)
EPA chemische Informationen
1 · 1,2-Butanediol (584-03-2)
UN Hazard Class: 3; UN Pack Group: III
EPA Safer ChemicalChemical: 1,2-Butanediol
Chemical DangersDecomposes on heating. Reacts vigorously with strong oxidants, reducing agents, acids and acid anhydrides.
NFPA Hazard Classification · 3 Einträge

1 - Materials that, under emergency conditions, can cause significant irritation.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesEye Irrit. 2A (74.7%)
Explosive Limits and PotentialExplosive limits , vol% in air: 1.8 - 15.7

Sicherheit und Schutzausrüstung

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep cylinder cool by spraying with water.
First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Safe StorageSeparated from incompatible materials. See Chemical Dangers. Ventilation along the floor.
Fire Fighting ProceduresALC FOAM.
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage DisposalCollect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures · 2 Einträge

... /IF/ AGITATED OR HEATED, OR IF SKIN CONTACT IS EXTENSIVE & PROLONGED, IT IS ADVISABLE TO PROTECT PERSONNEL BY ENCLOSING PROCESS OR PROVIDING LOCAL EXHAUST VENTILATION. /GLYCOLS & DERIV/

MAIN HAZARD ASSOC WITH THESE SUBSTANCES /IS/ THAT OF INGESTION /WHICH/ CAN USUALLY BE PREVENTED BY KEEPING THEM IN PROPERLY LABELLED CONTAINERS. /GLYCOLS & DERIV/

Eye PreventionWear safety spectacles.
Fire PreventionNO open flames. Above 93 °C use a closed system and ventilation.
Inhalation RiskNo indication can be given whether a harmful concentration in the air will be reached.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT GENERATION OF MISTS!

Toxikologische Informationen

Body BurdenNIOSH (NOES Survey 1981-1983) has statistically estimated that 1,821 workers are potentially exposed to 1,2-butanediol in the USA(1).
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: 1,2-Butanediol will probably biodegrade based on a screening test of the structurally analogous 1,4-butanediol(5,SRC). According to a suggested classification scheme(3), the estimated Koc value of 17(1,2) indicates that 1,2-butanediol will be very highly mobile in soil. Based on the vapor pressure of 0.0501 mm Hg at 25 °C(4), 1,2-butanediol is expected to volatilize if spilled on dry soil surfaces(SRC).

AQUATIC FATE: Based on the estimated Henry's Law constant of 2.3X10-7 atm-cu m/mole at 25 °C(3), 1,2-butanediol is expected to be essentially nonvolatile from water. Adsorption to sediment, bioconcentration in aquatic organisms, and hydrolysis are not expected to be important fate processes for 1,2-butanediol in water systems(SRC). 1,2-Butanediol is expected to biodegrade based on a screening test for 1,4-butanediol(SRC).

ATMOSPHERIC FATE: Based on the measured vapor pressure of 0.0501 mm Hg at 25 °C(1), 1,2-butanediol is expected to exist almost entirely in the vapor phase in the ambient atmosphere(2). Vapor phase 1,2-butanediol is degraded by reaction with photochemically formed hydroxyl radicals in the ambient atmosphere; the half-life for this reaction in air can be estimated to be about 25 hours(3,SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Signs and Symptoms · 3 Einträge

Dizziness. Drowsiness. Headache.

Redness. Pain.

Nausea. Abdominal pain. Diarrhoea. Aspiration hazard!

Effluent ConcentrationsAn unspecified isomer of butanediol was qualitatively identified as a volatile component at 1 of 5 hazardous waste sites(1).
ICSC Environmental DataEnvironmental effects of the substance have been adequately investigated, but no significant effects have been found.
Soil Adsorption/Mobility · 1 Eintrag

Based on an estimated log octanol-water partition coefficient of -0.29(2) and a recommended regression-derived equation(1), the Koc for 1,2-butanediol can be estimated to be 17(SRC). According to a suggested classification scheme(3), this Koc value indicates that 1,2-butanediol will be very highly mobile in soil(SRC).

Human Toxicity ExcerptsEYE CONTACT WITH 1,2-BUTANEDIOL MAY RESULT IN CORNEAL INJURY, BUT EVEN PROLONGED SKIN CONTACT IS USUALLY INNOCOUS WITH RESPECT TO PRIMARY IRRITATION & ABSORPTION TOXICITY. NO ADVERSE EFFECTS OF VAPOR INHALATION HAVE BEEN REPORTED.
Artificial Pollution Sources1,2-Butanediol may be released to the environment during its production, formulation and use as a solvent and chemical intermediate(1,SRC).
Environmental Biodegradation · 1 Eintrag

2-Butanol was shown to biologically oxidize to 1,2-butanediol in cell free extracts of Pseudomonas species(1). However, 1,2-butanediol was not converted using the same organism(1). Using an initial concn of 100 mg/L 1,4-butanediol, 74- 96 percent BOD was observed after a 2 week period in a biodegradation screening test using 30 mg/L sludge(2) and 1,2- butanediol is expected to behave similarly under the same conditions based on structural analogy to 1,4-butanediol(SRC).

Environmental Bioconcentration · 1 Eintrag

Based on an estimated log octanol-water partition coefficient of -0.29(2) and a recommended regression-derived equation(1), the BCF for 1,2-butanediol can be estimated to be 0.35(SRC). This BCF value indicates that 1,2-butanediol will not bioconcentrate in aquatic organisms(SRC).

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
1993
hs_code
29053995
RTECS-Nr.
EK0380000
safety_code
24/25
hazard_class
3
packing_group
III
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
584-03-2(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2
General Manufacturing Information1,2-Butanediol: ACTIVE

Anwendungen

Verwenden1,2-Butanediol was used in the synthesis of (R)-2-hydroxybutyric acid.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

1-BROMO-2-BUTANOL2-OXOBUTANALDEHYDE2-Hydroxypropanoic acidMethanolPropan-1,2-diol2,4-Diethyl-1,3,2-dioxaborolane

Ergänzende Hinweise

DefinitionChEBI: A butanediol in which the two hydroxy groups are located at positions 1 and 2.