Basic information
- CAS
558-37-2- Standard SMILES
C=CC(C)(C)C- InChIKey
PKXHXOTZMFCXSH-UHFFFAOYSA-N- Molecular formula
- C6H12
- Average molar mass
- 84.16 g/mol
- Monoisotopic mass
- 84.09390038
Names & identifiers
- Preferred name
- 3,3-Dimethyl-1-butene
- IUPAC
- 3,3-dimethylbut-1-ene
- English name
- 3,3-Dimethyl-1-butene
- Molecular formula
- C6H12
- Molecular weight
- 84.16
Names & synonyms
3,3-DIMETHYL-1-BUTENE558-37-2Neohexene3,3-Dimethylbut-1-enetert-Butylethylene1-Butene, 3,3-dimethyl-tert-Butylethenetert-HexeneTrimethylvinylmethane3,3-Dimethylbutene2,2-Dimethyl-3-butene3,3-Dimethy-1-butene
Show more names
(CH3)3CCH=CH23,3-DiMethylbut-1-en
UNII-01ZB73D2KKMFCD00008853NSC 7411901ZB73D2KKDTXSID1027211EINECS 209-195-93,3-Dimethyl-1-butene;NeohexeneNSC-74119
Database identifiers
- CAS
558-37-2- PubChem CID
- 11210
- DTXSID
DTXSID1027211- ChEMBL
CHEMBL3183368- UNII
- 01ZB73D2KK
- EC Number
- 209-195-9
- Nikkaji
- J38.822J
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 45.5
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aliphatics, Unsaturated
SpringerMaterials PropertiesCoriolis coupling
Vapor Pressure431.0 [mmHg]
Physical Description
Liquid
Colorless liquid; bp= 40-41 deg C; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- -115 °C · -115 °C (lit.)
- Boiling point
- 41 °C · 41 °C (lit.)
- Density
- 0.653 g/mL · 0.653 g/mL at 25 °C (lit.)
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 6.96 psi · 6.96 psi ( 20 °C)
- refractive index
- 20 · n20/D 1.376(lit.)
- Flash point
- 20 °F · −20 °F
- storage temp.
- 2 · 2-8°C
- form
- Liquid
- color
- Clear colorless
- explosive limit
- 1.2 % · 1.2%(V)
- Water Solubility
- Not miscible or difficult to mix in water.
- BRN
- 1697101 · 1697101
- Henry's Law Constant
- 2.8 · 2.8×10-5 mol/(m3Pa) at 25℃, Yaws (2003)
- InChI
- 1S/C6H12/c1-5-6(2,3)4/h5H,1H2,2-4H3
- InChIKey
- PKXHXOTZMFCXSH-UHFFFAOYSA-N
- SMILES
- CC(C)(C)C=C
- CAS DataBase Reference
- 558 · 558-37-2(CAS DataBase Reference)
- FDA UNII
- 1 ZB73D2KK · 01ZB73D2KK
- NIST Chemistry Reference
- 1 · 1-Butene, 3,3-dimethyl-(558-37-2)
- EPA Substance Registry System
- 1 · 1-Butene, 3,3-dimethyl- (558-37-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H304
- Precautionary statements
- 210 · P210-P233-P240-P241-P301+P310-P331
- PPE
- Eyeshields, Faceshields, Gloves
- Hazard Codes
- F,Xn,Xi
- Risk Statements
- 11 · 11-36/37/38-65
- Safety Statements
- 16 · 16-26-33-36-62-37/39
- RIDADR
- 3295 · UN 3295 3/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 8000000 · BS8000000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29012980 · 29012980
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 1 Flam · Asp. Tox. 1Flam. Liq. 2
- 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
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P331, 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 69 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1-Butene, 3,3-dimethyl-
1-Butene, 3,3-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butene, 3,3-dimethyl- 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)
3,3-Dimethyl-1-butene: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Depression noted in rats 1 hour after receiving 5 gm/kg by oral gavage; Rats were prostrate, but no rats died during inhalation exposure to 51,000 ppm for 4 hours; No evidence of skin sensitization in guinea pigs and no evidence of reproductive or developmental toxicity; [EPA ChAMP: C6 Summaries] An irritant; Harmful by ingestion (may cause lung damage by aspiration); [Alfa Aesar MSDS] See 3-Methyl-1-butene.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity DataLC50 (rat) = > 51,000 ppm/4hr
Safety data
- PPE
- Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BS8000000
- ridadr
- UN 3295 3/PG 2
- hs_code
- 29012980
- risk_code
- 11-36/37/38-65
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
- hazard_code
- F,Xn,Xi
- safety_code
- 16-26-33-36-62-37/39
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225-H304
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Asp. Tox. 1Flam. Liq. 2
- Precautionary statements
- P210-P233-P240-P241-P301+P310-P331
Chemistry & industry
Uses & manufacturing
UsesUsed as a chemical intermediate; [EPA ChAMP]
U.S. Production2023: 654,414 lb
Industry UsesFuel
General Manufacturing Information
Non-metallic Mineral Product Manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other non-metallic mineral product manufacturing)
1-Butene, 3,3-dimethyl-: ACTIVE
Applications
Uses3,3-Dimethyl-1-butene is a useful reagent for organic synthesis.
General Description3,3-Dimethyl-1-butene oxidizes selectively to corresponding epoxide by chlorine promoted Ag(111) oxygen adatoms. It undergoes copolymerization with ethylene using a chain-walking Pd-diimine catalyst.
Preparation methods
PreparationIn a 250 mL four-necked flask equipped with a mechanical stirrer, thermometer, and distillation column, 115 mL of N-methylpyrrolidone was added. The temperature was raised to 80 °C, and NaOH was added while stirring. Then, neohexane chloride was slowly added dropwise. The temperature was raised to 140–180 °C, and the fraction before 60 °C was collected. The organic phase was separated, and the fraction before 50 °C was redistilled, yielding 82.2% and 99% purity of 3,3-dimethyl-1-butene. The solvent was recovered five times after filtration, and the reaction yield remained above 70%. Boiling point: 30–50 °C.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
18 records
Compound notes
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