3,3-Dimethyl-1-butyne (HCID 13512)

Overview

inhibits cytochrome P450 2E1 T303A; structure in first source

Names & identifiers

Preferred name: 3,3-Dimethyl-1-butyne
IUPAC: 3,3-dimethylbut-1-yne
English name: 3,3-Dimethyl-1-butyne
Molecular formula: C6H10
Molecular weight: 82.14

Names & synonyms

3,3-Dimethyl-1-Butyne917-92-03,3-DIMETHYLBUTYNEt-butyl acetylene3,3,3-TrimethylpropyneDTXSID70238671RefChem:90801DTXCID20161162213-035-33,3-dimethylbut-1-ynetert-Butylacetylenet-Butylacetylene

Show more names

3,3-dimethyl-but-1-yneNeohexyne-1-butynet-butylacetyene(CH3)3CCequivCH

1-Butyne, 3,3-dimethyl-MFCD00008852tert-ButylethynePX4NL23U52CHEMBL190822151730-68-81-BUTYNE,3,3-DIMETHYL-3,3-Dimethylbutyne-1

Database identifiers

CAS: 917-92-0
PubChem CID: 13512
DTXSID: DTXSID70238671
ChEMBL: CHEMBL1908221
UNII: PX4NL23U52
EC Number: 213-035-3
Nikkaji: J132.792E

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 1
Heavy atoms: 6
Formal charge: 0
Complexity: 73.9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aliphatics, Unsaturated

SpringerMaterials PropertiesSchoenflies notation

Vapor Pressure398.0 [mmHg]

Physical DescriptionColorless liquid; Boiling point = 37-38 deg C; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: -78 °C · -78 °C (lit.)
Boiling point: 37 · 37-38 °C (lit.)
Density: 0.667 g/mL · 0.667 g/mL at 25 °C (lit.)
vapor pressure: 7.88 psi · 7.88 psi ( 20 °C)
refractive index: 20 · n20/D 1.374(lit.)
Flash point: 30 °F · <−30 °F
storage temp.: 2 · 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Liquid
color: Clear colorless
PH: 7.51 at · 7.51 at 24.8℃ and 10g/L
Water Solubility: Miscible with chloroform, benzene and toluene. Immiscible with water.
BRN: 1697100 · 1697100
Henry's Law Constant: 4.6 · 4.6×10-4 mol/(m3Pa) at 25℃, Yaws (2003)
Stability: Stable, but highly flammable. Readily forms explosive mixtures with air. Note low flash point.
InChI: 1S/C6H10/c1-5-6(2,3)4/h1H,2-4H3
InChIKey: PPWNCLVNXGCGAF-UHFFFAOYSA-N
SMILES: CC(C)(C)C#C
CAS DataBase Reference: 917 · 917-92-0(CAS DataBase Reference)
FDA UNII: 4 NL23U52 · PX4NL23U52
NIST Chemistry Reference: 1 · 1-Butyne, 3,3-dimethyl-(917-92-0)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Danger
Hazard statements: 225 · H225-H412
Precautionary statements: 210 · P210-P233-P240-P241-P242-P273
PPE: Eyeshields, Faceshields, Gloves
Hazard Codes: F+,Xi
Risk Statements: 12 · 12-36/37/38
Safety Statements: 3 · 3-16-26-33-7/9
RIDADR: 3295 · UN 3295 3/PG 2
WGK Germany: 3 · 3
HazardClass: 3 · 3
PackingGroup: I
HS Code: 29012990 · 29012990
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 Flam · Aquatic Chronic 3Flam. Liq. 2
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H224 (71.9%): Extremely flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, 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 57 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12565

1-Butyne, 3,3-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; Harmful by ingestion (may cause lung damage by aspiration); [Alfa Aesar MSDS] See 1-Butyne.

Hazard Classes and CategoriesFlam. Liq. 1 (71.9%)

Safety data

PPE: Eyeshields, Faceshields, Gloves
wgk: 3
ridadr: UN 3295 3/PG 2
hs_code: 29012990
risk_code: 12-36/37/38
Signal word: Danger
Symbol(GHS): GHS02
hazard_code: F+,Xi
safety_code: 3-16-26-33-7/9
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: I
Hazard statements: H225-H412
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Aquatic Chronic 3Flam. Liq. 2
Precautionary statements: P210-P233-P240-P241-P242-P273

Chemistry & industry

Applications · 2 items

Description3,3-Dimethyl-1-butyne is a colourless liquid that is soluble in most organic solvents and readily reacts with air. It is a reactive intermediate that can be synthesised from cyclopentene oxide. This molecule possesses an acidic hydrogen atom on the methyl group and a nucleophilic hydrogen atom on the butyl group. The reaction mechanism is believed to involve a nucleophilic attack by the nucleophile on the acidic hydrogen atom, thereby initiating a substitution reaction. The activation energy is relatively low due to the non-polar solvent and polar reactants involved in this process.

Uses3,3-Dimethyl-1-butyne is used as an active pharmaceutical intermediate for terbinafine. It is also used in the preparation of 2,2,7,7-tetramethyl-octa-3,5-diyne. Further, it is used in the synthesis of erythro and threo isomers of B-(3,3-dimethyl-1,2-dideuterio-1-butyl)-9-BBN by hydroboration-deuteronolysis-hydroboration sequence.