2-methylpropyl chloroformate

• ChemBase ID: 103332
• Molecular Formular: C5H9ClO2
• Molecular Mass: 136.57676
• Monoisotopic Mass: 136.02910721
• SMILES: CC(C)COC(=O)Cl
• Canonical SMILES: CC(COC(=O)Cl)C
• InChI: InChI=1S/C5H9ClO2/c1-4(2)3-8-5(6)7/h4H,3H2,1-2H3
• InChIKey: YOETUEMZNOLGDB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methylpropyl chloroformate
• IUPAC Traditional name: 2-methylpropyl chloroformate
• Synonyms: isobutyl carbonochloridate; Chloroformic acid isobutyl ester; IBCF; Isobutyl chloroformate; Carbonochloridic acid, 2-methylpropyl ester; Chlorameisensaurebutylester; i-Butyl chloroformate; ISOBUTYL CHLOROFORMATE; 氯甲酸异丁酯

Database IDs

• CAS Number: 543-27-1
• EC Number: 208-840-1
• MDL Number: MFCD00000642
• Beilstein Number: 956590
• Merck Index: 145139
• PubChem SID: 162090671; 24853864; 24850706
• PubChem CID: 62365

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.1735783
• LogD (pH = 7.4): 2.1735783
• Log P: 2.1735783
• Molar Refractivity: 31.87 cm^3
• Polarizability: 12.658829 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -80°C
• Boiling Point: 128°C; 128.8 °C(lit.); 128-129°C
• Flash Point: 27.7°C; 30°C(86°F); 36 °C; 96.8 °F
• Density: 1.04 g/ml; 1.045 g/mL at 20 °C; 1.048; 1.053 g/mL at 25 °C(lit.)
• Refractive Index: 1.4060; n20/D 1.407(lit.); n20/D 1.408
• Vapor Pressure: 0.33 mmHg ( 20 °C); 0.33 psi @ 20°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Toxic (T)
• UN Number: 2742; 3390; UN2742
• German water hazard class: 2
• Hazard Class: 3/8; 6.1
• Packing Group: 1; I; II
• Australian Hazchem: 3W
• Risk Statements: 10-22-23-34; 10-23/24/25-34; R:10-25-34
• Safety Statements: 26-36/37/39-45; 9-23-26-27-36/37/39-45-60; S:16-28-36/37/39-45
• EU Classification: TFC
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 155
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H314-H331; H300-H310-H330-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3390 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: ClCO2CH2CH(CH3)2

DETAILS

MP Biomedicals - 02151355

Reagent used in mixed anhydride method of peptide synthesis.
1 ml = approx. 1.04 g

MP Biomedicals - 05202510

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 177989

Packaging
25, 100 g in Sure/Seal™
Application
Derivatizing reagent for GC analysis of amino acids1 and amines.2 Peptide coupling agent.3

REFERENCES

• Superior to ethyl chloroformate in the mixed anhydride method of peptide synthesis: Org. Prep. Proced. Int., 7, 215 (1975); review: Org. React., 12, 157 (1962). Use in combination with 1-Methylpiperidine, L03398, minimizes competing urethane formation, arising from cleavage of the mixed anhydride in the wrong sense: J. Org. Chem., 48, 2939 (1983). Addition of CuCl₂ is reported to suppress racemization completely: Chem. Lett., 2125 (1989). For peptide reagents, see Appendix 6.
• Has been used to protect a nucleoside OH group as its isobutyl carbonate. Cleavage was by hydrolysis with 80% AcOH: J. Org. Chem., 32, 2365 (1967). Protection of amino groups as their isobutyl carbamates has also been reported: J. Am. Chem. Soc., 91, 3356 (1969).