Basic information
- Standard SMILES
C#CC(C)(C)O- InChIKey
CEBKHWWANWSNTI-UHFFFAOYSA-N- Molecular formula
- C5H8O
- Average molar mass
- 84.12 g/mol
- Monoisotopic mass
- 84.05751488
Overview
2-methyl-2-hydroxy-3-butyne is a colorless to straw yellow liquid. (USCG, 1999)
Names & identifiers
- Preferred name
- 2-Methyl-3-butyn-2-ol
- IUPAC
- 2-methylbut-3-yn-2-ol
- English name
- 3-Methyl butynol
- Molecular formula
- C5H8O
- Molecular weight
- 84.12
Names & synonyms
Show more names
Database identifiers
- CAS
115-19-5- PubChem CID
- 8258
- DTXSID
DTXSID2021949- ChEMBL
CHEMBL3185871- UNII
- EHB904XHKH
- EC Number
- 204-070-5
- Nikkaji
- J38.146B
Properties
Computed structural properties
- XLogP
- 0.3
- 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
- 83.4
Experimental & physicochemical properties
LogP
0.318
0.28
Density
0.8672 (USCG, 1999) - Less dense than water; will float
Density (gas): 0.9 kg/m³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.04
Flash Point
77 °F (USCG, 1999)
20 °C c.c.
Boiling Point
219.2 to 221 °F at 760 mmHg (USCG, 1999)
104-105 °C
Melting Point
36.7 °F (USCG, 1999)
2.6 °C
Vapor Pressure
16.0 [mmHg]
Vapor pressure, kPa at 20 °C: 2
Physical Description
2-methyl-2-hydroxy-3-butyne is a colorless to straw yellow liquid. (USCG, 1999)
Liquid; mp = 2.6 deg C; [Merck Index] Colorless liquid; [Alfa Aesar MSDS]
COLOURLESS LIQUID.
Physicochemical properties
- Melting point
- 3 °C · 3 °C
- Boiling point
- 104 °C · 104 °C(lit.)
- Density
- 0.868 g/mL · 0.868 g/mL at 25 °C(lit.)
- vapor pressure
- 15 mm · 15 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.42(lit.)
- Flash point
- 77 °F · 77 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Fully miscible.
- form
- Powder or Crystals
- pka
- 13.34 · 13.34±0.29(Predicted)
- color
- White to yellow-beige to brown
- PH
- 7 · 7 (H2O, 20℃)
- explosive limit
- 1.8 · 1.8-16%(V)
- Water Solubility
- miscible
- Merck
- 14 · 14,6034
- BRN
- 635746 · 635746
- Henry's Law Constant
- 2.5 · 2.5×100 mol/(m3Pa) at 25℃, Altschuh et al. (1999)
- Stability
- Stable. Flammable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3
- InChIKey
- CEBKHWWANWSNTI-UHFFFAOYSA-N
- SMILES
- CC(C)(O)C#C
- LogP
- 0.318 at · 0.318 at 20-25℃
- CAS DataBase Reference
- 115 · 115-19-5(CAS DataBase Reference)
- FDA UNII
- 904 XHKH · EHB904XHKH
- NIST Chemistry Reference
- 3 · 3-Butyn-2-ol, 2-methyl-(115-19-5)
- EPA Substance Registry System
- 2 · 2-Methyl-3-butyn-2-ol (115-19-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H318-H361-H336-H226
- Precautionary statements
- 501 · P501-P270-P202-P240-P261-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P313-P303+P361+P353-P301+P312+P330-P304+P340+P312-P305+P351+P338+P310-P403+P233-P403+P235-P405
- target organs
- Central nervous system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn
- Risk Statements
- 10 · 10-22-41
- Safety Statements
- 26 · 26-39-16
- RIDADR
- 1987 · UN 1987 3/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 810000 · ES0810000
- Autoignition Temperature
- 662 °F · 662 °F
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29052990 · 29052990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Repr. 2STOT SE 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1420 mg/kg LD50 dermal Rat > 2000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 4.8% (24 of 500) of reports.
Danger
H225 (62.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 500 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: 3-Butyn-2-ol, 2-methyl-
Status: Active Update: 18-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12665
3-Butyn-2-ol, 2-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Special Hazards of Combustion Products: Irritating and toxic gases, such as carbon dioxide and carbon monoxide, may be produced in fire. (USCG, 1999)
Highly flammable. Vapour/air mixtures are explosive. Risk of explosion on contact with copper.
Hazards Summary
An eye but not skin irritant in rabbits; Not a skin sensitizer in guinea pig modified split adjuvant test; Developmental toxicity observed in rats at doses maternally toxic; [IUCLID] Causes somnolence, lung changes, ataxia, respiratory depression, and general anesthesia in inhalation lethal-concentration studies of mice; Oral LD50 (mouse) = 500 mg/kg; [RTECS] A skin and eye irritant; May cause smarting and reddening of skin if spilled and allowed to remain on clothes; High vapor concentrations may cause mild smarting of eyes and respiratory tract; [CHRIS] An eye irritant; [ICSC] May cause serious eye injury; Harmful by ingestion; [ECHA REACH Registrations] An irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Reactivity Profile
2-METHYL-2-HYDROXY-3-BUTYNE is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Safety & protection
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water.
Use carbon dioxide, foam, dry powder. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact of the substance with water.
First Aid Measures
Fresh air, rest.
Rinse skin with plenty of water or shower.
Rinse with plenty of water (remove contact lenses if easily possible).
Rinse mouth.
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Toxicology
Signs and Symptoms
Cough.
Redness. Pain.
Dizziness.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- ES0810000
- ridadr
- UN 1987 3/PG 2
- hs_code
- 29052990
- Toxicity
- LD50 orally in Rabbit: 1420 mg/kg LD50 dermal Rat > 2000 mg/kg
- risk_code
- 10-22-41
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 26-39-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Central nervous system
- Hazard statements
- H302-H318-H361-H336-H226
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Flam. Liq. 2Repr. 2STOT SE 3
- Autoignition Temperature
- 662 °F
- Precautionary statements
- P501-P270-P202-P240-P261-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P313-P303+P361+P353-P301+P312+P330-P304+P340+P312-P305+P351+P338+P310-P403+P233-P403+P235-P405
Chemistry & industry
Uses & manufacturing
Uses
Has been used as a pheromone substitute in beetle control; [REPROTOX] Used as an intermediate, laboratory reagent, and in wood treatment; [ECHA REACH Registrations]
Applying Wood Preservatives [Category: Other]
Applications
UsesStabilizer in chlorinated solvents, viscosity reducer and stabilizer, electroplating brightener, intermediate.
Uses2-Methyl-3-butyn-2-ol is used as an intermediate in the manufacture of products for the agrochemical and specialty chemical industry.
General DescriptionColorless to straw yellow liquid.
Preparation methods
Preparation3-Methyl butynol is produced from Acetone and Acetylene in liquid Ammonia with Sodamide (or in Cellosolve with Potassium hydroxide). The process yields Methylbutynol which can be hydrogenated to Methylbutenol.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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