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157422

Sigma-Aldrich

Isovaleryl chloride

98%

Synonym(s):

3-Methylbutyryl chloride

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About This Item

Linear Formula:
(CH3)2CHCH2COCl
CAS Number:
108-12-3
Molecular Weight:
120.58
Beilstein:
741910
EC Number:
203-552-2
MDL number:
MFCD00000738
UNSPSC Code:
12352100
PubChem Substance ID:
24849677
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.416 (lit.)

bp

115-117 °C (lit.)

density

0.989 g/mL at 25 °C (lit.)

functional group

acyl chloride

SMILES string

CC(C)CC(Cl)=O

InChI

1S/C5H9ClO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3

InChI key

ISULZYQDGYXDFW-UHFFFAOYSA-N

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Application

Isovaleryl chloride was used in the synthesis of:
  • furanodictines A and B
  • tetrapeptide amide, S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide
  • (+)-blastmycinone
  • (R)- and (S)-2-methyl-4-octanol, aggregation pheromone of some sugarcane weevils

Signal Word

Danger

Hazard Statements

H226,H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBR3526V
BCBG8712V
BCBF9392V
BCBB1676V
BCBB1676

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The Synthesis of the Tetrapeptide Amide S-Benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide
Ressler Cand Vincent du Vigneaud.
Journal of the American Chemical Society, 76(12), 3107-3109 (1954)
Makoto Ogata et al.
Carbohydrate research, 345(2), 230-234 (2009-12-08)
A novel synthesis of furanodictines A [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (GlcNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acetamido-3,6-anhydro-2-deoxy-D-mannofuranose (5)] from GlcNAc. Reaction with borate
Organoaluminium induced ring-opening of epoxypyranosides. V. Formal total synthesis of antimycin A3 and synthesis of (+)-blastmycinone.
Inghardt T and Frejd T.
Tetrahedron, 47(32), 6483-6492 (1991)
Enantioselective synthesis of (R)-and (S)-2-methyl-4-octanol, the male-produced aggregation pheromone of Curculionidae species.
Baraldi PT, et al.
Tetrahedron Asymmetry, 13(6), 621-624 (2002)
Jessica L Wojtaszek et al.
Cell, 178(1), 152-159 (2019-06-11)
Intrinsic and acquired drug resistance and induction of secondary malignancies limit successful chemotherapy. Because mutagenic translesion synthesis (TLS) contributes to chemoresistance as well as treatment-induced mutations, targeting TLS is an attractive avenue for improving chemotherapeutics. However, development of small molecules with
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