3-chloro-3-methylbut-1-yne

• ChemBase ID: 76842
• Molecular Formular: C5H7Cl
• Molecular Mass: 102.56208
• Monoisotopic Mass: 102.0236279
• SMILES: ClC(C#C)(C)C
• Canonical SMILES: C#CC(Cl)(C)C
• InChI: InChI=1S/C5H7Cl/c1-4-5(2,3)6/h1H,2-3H3
• InChIKey: QSILYWCNPOLKPN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-chloro-3-methylbut-1-yne
• IUPAC Traditional name: 1-butyne, 3-chloro-3-methyl-
• Synonyms: 3-Chloro-3-methyl-1-butyne; 3-Chloro-3-methylbut-1-yne; 1,1-Dimethylpropargyl chloride; 3-氯-3-甲基-1-丁炔

Database IDs

• CAS Number: 1111-97-3
• EC Number: 214-188-9
• MDL Number: MFCD00190221
• PubChem SID: 24858181; 162041744
• PubChem CID: 70679

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.7612495
• LogD (pH = 7.4): 1.7612495
• Log P: 1.7612495
• Molar Refractivity: 27.9495 cm^3
• Polarizability: 10.666419 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -61 °C(lit.); -61°C
• Boiling Point: 73-75 °C(lit.); 73-75°C
• Flash Point: 39.2 °F; 4 °C; 4°C(40°F)
• Density: 0.913; 0.913 g/mL at 25 °C(lit.)
• Refractive Index: 1.4178; n20/D 1.418(lit.)

Safety Information

• Storage Warning: Irritant/Highly Flammable
• European Hazard Symbols: Flammable (F); Irritant (Xi); Harmful (Xn)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-20/21/22; 11-36/37/38
• Safety Statements: 16-26-29-33-37; 16-26-36
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H332; H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%
• Linear Formula: ClC(CH3)2C≡CH

DETAILS

Sigma Aldrich - 301345

Packaging
5, 25 g in ampule

REFERENCES

• Reagent for an improved 2-step introduction of the 1,1-dimethylallyl (DMA) ester protecting group for carboxylic acids. Reaction with the acid in the presence of copper(I) iodide and cesium carbonate in DMF affords the 1,1-dimethylpropargyl ester. Hydrogenation with Pd/barium sulfate/quinoline affords the 1,1-dimethylallyl ester. The DMA group is resistant to nucleophilic attack, but readily cleaved under non-acidic conditions with Pd(0), which is an advantage compared with the tert-butyl ester in solid-phase peptide synthesis: Org. Lett., 7, 1473 (2005).