3-Methyl-2-buten-1-OL
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Basic information
- CAS
556-82-1- Standard SMILES
CC(C)=CCO- InChIKey
ASUAYTHWZCLXAN-UHFFFAOYSA-N- Molecular formula
- C5H10O
- Average molar mass
- 86.13 g/mol
- Monoisotopic mass
- 86.07316494
Overview
Prenol is a member of prenols and an alkenyl alcohol.
Names & identifiers
- Preferred name
- 3-Methyl-2-buten-1-OL
- IUPAC
- 3-methylbut-2-en-1-ol
- English name
- 3-Methyl-2-buten-1-ol
- Molecular formula
- C5H10O
- Molecular weight
- 86.13
Names & synonyms
3-METHYL-2-BUTEN-1-OL556-82-1Prenol3-Methylbut-2-en-1-olPrenyl alcohol2-Buten-1-ol, 3-methyl-3-Methyl-2-butenolDimethylallyl alcohol3-Methyl-2-butenyl alcoholFEMA No. 3647DTXSID20272062-methyl-2-buten-4-ol
Show more names
ISOPENTENOL3-METHYL-2-BUTENE-1-OLFEMA 3647ISOPENTENYL ALCOHOLISOBUTENYLCARBINOL
55MY0HM445NSC-158709DTXCID507206CHEBI:16019RefChem:175877gamma,gamma-Dimethylallyl alcohol209-141-43,3-Dimethylallyl alcohol
Database identifiers
- CAS
556-82-1- PubChem CID
- 11173
- DTXSID
DTXSID2027206- ChEMBL
CHEMBL3184952- ChEBI
CHEBI:16019- UNII
- 55MY0HM445
- EC Number
- 209-141-4
- Nikkaji
- J11.528B
Properties
Computed structural propertiesFilling in
- XLogP
- 1
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 51
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (3-Methyl-2-buten-1-ol) -> IFRA transparency List
LogP0.91
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
0.85 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.1
0.844-0.852
Flavoring AgentsEU Flavoring substances
Viscosity3.5 mm²/s at 25 °C
Solubility
Solubility in water, g/100ml at 20 °C: 17 (good)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1853 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H226: Flammable liquid and vapor [Warning Flammable liquids]
Hazard information
Regulatory Information
Chemical: 2-Buten-1-ol, 3-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 23-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/1947
3-Methyl-2-buten-1-ol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Buten-1-ol, 3-methyl-: Human health tier I assessment
Fire HazardsFlammable. Above 50 °C explosive vapour/air mixtures may be formed.
Hazards Summary
A moderate skin irritant; [RTECS] A severe skin and eye irritant; [ICSC] Safe when used as a flavoring agent in food; [JECFA] Causes burns; Harmful by ingestion; [ECHA REACH Registrations] A skin and strong eye irritant; Toxic by ingestion; [Alfa Aesar MSDS]
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA] Used as an intermediate for citral and in cosmetics; [OECD SIDS: IUCLID Data Set]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information2-Buten-1-ol, 3-methyl-: ACTIVE
Applications
Description3-Methyl-2-buten-l-ol has a phenolic, metallic odor bearing a resemblance to iron gallate ink. May be synthesized from isoprene by hydration via prenyl acetate or by rearrangement of 3-methyll-buten-3-ol.
Uses3-Methyl-2-buten-1-ol is used as a reagent for protection of carboxylic acids as their 3-methyl-2-buten-1-yl (Prenyl) esters. It is also used in perfumery.
Uses3-Methyl-2-buten-1-ol was used as starting reagent during asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone via Sharpless asymmetric epoxidation reaction.
General Description3-Methyl-2-buten-1-ol reacts with nitrosocarbonyl benzene to yield 5-hydroxy-isoxazolidines. It is commonly used as fragrance ingredient.
Upstream & downstream products
Upstream raw materials
Related reactions
151 records
Compound notes
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