Basic information
- 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 properties
- 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)
Insoluble in water; soluble in fats
soluble (in ethanol)
Flash Point50 °C c.c.
Boiling Point
138.00 to 174.00 °C. @ 760.00 mm Hg
140 °C
140 °C
Physicochemical properties
- Melting point
- 43.52 °C · 43.52°C
- Boiling point
- 140 °C · 140 °C(lit.)
- Density
- 0.848 g/mL · 0.848 g/mL at 25 °C(lit.)
- vapor pressure
- 1.4 mm · 1.4 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.443(lit.)
- FEMA
- 3647 · 3647 | 3-METHYL-2-BUTEN-1-OL
- FLAVIS Number
- 2.109 · 02.109 | 3-Methylbut-2-en-1-ol
- Flash point
- 110 °F · 110 °F
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 64 g/l · 64g/l
- form
- Liquid
- pka
- 14.83 · 14.83±0.10(Predicted)
- color
- Clear colorless to very slightly yellow
- Odor
- 100 % · at 100.00 %. fruity green lavender
- Odor Type
- fruity
- biological source
- synthetic
- explosive limit
- 2.7 · 2.7-16.3%(V)
- Water Solubility
- 170 g/L · 170 g/L (20 ºC)
- JECFA Number
- 1200 · 1200
- BRN
- 1633479 · 1633479
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3
- InChIKey
- ASUAYTHWZCLXAN-UHFFFAOYSA-N
- SMILES
- C\C(C)=C\CO
- LogP
- 1.24 · 1.24
- CAS DataBase Reference
- 556 · 556-82-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · 3-METHYL-2-BUTEN-1-OL
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 55 MY0HM445 · 55MY0HM445
- NIST Chemistry Reference
- 2 · 2-Buten-1-ol, 3-methyl-(556-82-1)
- EPA Substance Registry System
- 2 · 2-Buten-1-ol, 3-methyl- (556-82-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 226 · H226-H302+H332-H314-H335
- Precautionary statements
- 210 · P210-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn
- Risk Statements
- 10 · 10-22-36/37/38-38-21/22
- Safety Statements
- 26 · 26-36-37-23-16
- RIDADR
- 1987 · UN 1987 3/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 9472500 · EM9472500
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29052990 · 29052990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1BSTOT SE 3
- REACH Registrations
- Active
- 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
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
Chemical DangersDecomposes on heating. This produces irritating fumes.
Physical DangersThe vapour is heavier than air.
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flammable liquids - Category 3
Explosive Limits and PotentialExplosive limits , vol% in air: 2.7-16.3
Safety & protection
Fire FightingUse foam, carbon dioxide, dry powder, water in large amounts. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Seek medical attention if you feel unwell.
First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
Safe StorageFireproof. Keep in a well-ventilated room. Well closed. Store in an area without drain or sewer access.
Spillage Disposal
Personal protection: protective gloves and safety goggles. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. Cover the spilled material with non-combustible.
Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames, NO sparks and NO smoking. Above 50 °C use a closed system, ventilation and explosion-proof electrical equipment.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT GENERATION OF MISTS!
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation, local exhaust or breathing protection.
Effects of Short Term ExposureThe substance is severely irritating to the skin and eyes.
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by ingestion and by inhalation of its vapour.
Signs and Symptoms
Sore throat. Cough.
Redness. Pain.
Redness. Pain.
Sore throat.
ICSC Environmental DataThe substance is harmful to aquatic organisms.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- EM9472500
- ridadr
- UN 1987 3/PG 3
- hs_code
- 29052990
- risk_code
- 10-22-36/37/38-38-21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07
- hazard_code
- Xn
- safety_code
- 26-36-37-23-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H226-H302+H332-H314-H335
- 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
- Active
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1BSTOT SE 3
- Precautionary statements
- P210-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
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
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: Prenol is an alkenyl alcohol and a member of prenols.
Related reactions
151 records
Linked notes
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