2,2-dimethylpropanoyl chloride

• ChemBase ID: 103485
• Molecular Formular: C5H9ClO
• Molecular Mass: 120.57736
• Monoisotopic Mass: 120.03419259
• SMILES: CC(C)(C)C(=O)Cl
• Canonical SMILES: ClC(=O)C(C)(C)C
• InChI: InChI=1S/C5H9ClO/c1-5(2,3)4(6)7/h1-3H3
• InChIKey: JVSFQJZRHXAUGT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethylpropanoyl chloride
• IUPAC Traditional name: 2,2-dimethylpropanoyl chloride
• Synonyms: Pivaloyl chloride; Pivaloyl chloride; Trimethylacetyl chloride; Trimethylacetyl chloride; PIVALOYL CHLORIDE; 新戊酰氯; 三甲基乙酰氯; 新戊酰氯; 三甲基乙酰氯

Database IDs

• CAS Number: 3282-30-2
• EC Number: 221-921-6
• MDL Number: MFCD00000709
• Beilstein Number: 385668
• PubChem SID: 24900440; 162103128; 24887589
• PubChem CID: 62493

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.1095204
• LogD (pH = 7.4): 2.1095204
• Log P: 2.1095204
• Molar Refractivity: 30.2046 cm^3
• Polarizability: 11.899294 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -57°C
• Boiling Point: 105-106 °C(lit.); 105-106°C; 105-106°C
• Flash Point: 19 °C; 66.2 °F; 8.8°C; 8°C(46°F)
• Density: 0.979 g/ml; 0.979 g/mL at 25 °C(lit.); 0.980 g/mL at 20 °C; 0.985
• Refractive Index: 1.4120; n20/D 1.412; n20/D 1.412(lit.)
• Vapor Pressure: 36 mmHg ( 20 °C)
• Vapor Density: >1 (vs air)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Highly toxic (T+)
• UN Number: 2438; UN2438
• German water hazard class: 1
• Hazard Class: 3/8; 6.1
• Packing Group: 1; I; Truck Only
• Australian Hazchem: 2WE
• Risk Statements: 11-14-22-26-34; R:11-35
• Safety Statements: 16-26-36/37/39-45; 4-8-9-16-20-23-26-28-30-33-36/37/39-45; S:16-27/28-29-36/37/39-45
• EU Classification: TF1
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 132
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H330-H314-H318; H225-H302-H314-H330
• GHS Precautionary statements: P210-P260-P280-P284-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2438 6.1/PG 1
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: ≥98.0% (GC); 98+%; 99%
• Grade: purum
• Linear Formula: (CH3)3CCOCl

DETAILS

MP Biomedicals - 02151905

Reagent for mixed anhydride peptide synthesis.
1 ml = approx. 0.98 g

Sigma Aldrich - T72605

Packaging
5, 100, 500 mL in glass bottle
Application
Widely used N-acylating agent for amines,1 Schiff bases,2 and pyrrolidinones3 as well as O-acylating agent for alcohols,4 lactones,5 and saccharides.6

REFERENCES

• In the presence of Cu(I) halides, reacts with Grignard and organolithium reagents to give t-butyl ketones: Tetrahedron Lett., 829 (1971).
• Activates heteroaromatic amines to ring-lithiation. For example: Synthesis, 670 (1986):
  
• Reacts with sodium formate to give the mixed formic pivalic anhydride, a highly effective reagent for N-formylation: Rec. Trav. Chim., 101, 460 (1982). Similarly, has been used to form mixed anhydrides, particularly of N-protected amino acids and peptides, prior to coupling: Coll. Czech. Chem. Commun., 27, 1273 (1962). The sterically-hindered nature of the pivaloyl group greatly reduces attack at the 'wrong' carbonyl group. For peptide reagents, see Appendix 6.
• Has also been used as a reagent for protection of alcohols as their pivaloyl (Pv) esters, allowing selective acylation of a primary over a secondary alcohol: Synthesis, 453 (1986); selective protection of the less hindered of two primary alcohols is possible: J. Chem. Soc., Chem. Commun., 354 (1988). See also Trimethylacetic anhydride, B22983. Cleavage is by room temperature basic hydrolysis: Tetrahedron Lett., 317 (1973); 3561 (1979); J. Org. Chem., 42, 918 (1977), or methanolysis: J. Am. Chem. Soc., 112, 3693 (1990), or a number of other methods, including aqueous methylamine: Tetrahedron, 24, 639 (1968).