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19270

Sigma-Aldrich

Butyric anhydride

purum, ≥97.0% (NT)

Synonym(s):

Butanoic anhydride

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About This Item

Linear Formula:
(CH3CH2CH2CO)2O
CAS Number:
106-31-0
Molecular Weight:
158.19
Beilstein:
1099474
EC Number:
203-383-4
MDL number:
MFCD00009389
UNSPSC Code:
12352100
PubChem Substance ID:
329751708
NACRES:
NA.22

vapor density

5.45 (vs air)

Quality Level

100

vapor pressure

10 mmHg ( 79.5 °C)

grade

purum

Assay

≥97.0% (NT)

autoignition temp.

535 °F

expl. lim.

1.1 %, 104 °F
7.6 %, 144 °F

refractive index

n20/D 1.413 (lit.)
n20/D 1.413

bp

198-199 °C (lit.)

mp

−75-−66 °C (lit.)

solubility

alcohol: soluble (with decomposition)(lit.)
diethyl ether: soluble(lit.)
water: soluble (with decomposition)(lit.)

density

0.967 g/mL at 25 °C (lit.)

functional group

anhydride
ester

SMILES string

CCCC(=O)OC(=O)CCC

InChI

1S/C8H14O3/c1-3-5-7(9)11-8(10)6-4-2/h3-6H2,1-2H3

InChI key

YHASWHZGWUONAO-UHFFFAOYSA-N

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Application

Butyric anhydride was used in the synthesis of:
  • dibutyrylchitin, a lipophilic chitin diester
  • N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-n-butyramide
  • butyric-ester derivatives of hyaluronic acid

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM8557V
BCBF2703V
BCBC2594V
BCBC2594
1394425

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D Coradini et al.
International journal of cancer, 81(3), 411-416 (1999-04-21)
The potential clinical utility of sodium butyrate, a natural compound known to inhibit tumor-cell growth, is hampered by the difficulty of achieving effective in-vivo concentrations. The short half-life (about 5 minutes) of sodium butyrate results in rapid metabolism and excretion.
J J Kaylor et al.
Carbohydrate research, 331(4), 439-444 (2001-06-12)
The syntheses of four analogues of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-beta-D-glucopyranosylamine. n-Butyric anhydride gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N1-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-aminopropionamide. Succinimidyl
Xiaoning Shan et al.
International journal of pharmaceutics, 590, 119884-119884 (2020-09-21)
Poly(2-methyl-2-oxazoline) (PMOZ), poly(2-propyl-2-oxazoline) (PnPOZ) and poly(2-isopropyl-2-oxazoline) (PiPOZ) were synthesized by hydrolysis of 50 kDa poly(2-ethyl-2-oxazoline) (PEOZ) and subsequent reaction of the resulting poly(ethylene imine) with acetic, butyric and isobutyric anhydrides, respectively. These polymers were characterized by proton nuclear magnetic resonance, FTIR
Luca Casettari et al.
Drug development and industrial pharmacy, 38(8), 979-984 (2011-11-30)
Dibutyrylchitin (DBC), a lipophilic chitin diester, has been synthesized from chitin and butyric anhydride with methanesulfonic acid as catalyst. Exhaustive esterification of free alcoholic groups of chitin was assessed by FT-IR and (1)H-NMR spectroscopy. High degree of alkyl substitution allowed

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