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290890

Sigma-Aldrich

Dibutyltin diacetate

technical grade

Synonym(s):

Diacetoxydibutyltin

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About This Item

Linear Formula:
(CH3CH2CH2CH2)2Sn(OCOCH3)2
CAS Number:
1067-33-0
Molecular Weight:
351.03
Beilstein:
4136035
EC Number:
213-928-8
MDL number:
MFCD00008697
UNSPSC Code:
12352103
PubChem Substance ID:
24857495
NACRES:
NA.22

grade

technical grade

vapor density

12 (vs air)

vapor pressure

1.3 mmHg ( 25 °C)

refractive index

n20/D 1.471 (lit.)

bp

142-145 °C/10 mmHg (lit.)

mp

7-10 °C (lit.)

density

1.32 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(OC(C)=O)OC(C)=O

InChI

1S/2C4H9.2C2H4O2.Sn/c2*1-3-4-2;2*1-2(3)4;/h2*1,3-4H2,2H3;2*1H3,(H,3,4);/q;;;;+2/p-2

InChI key

JJLKTTCRRLHVGL-UHFFFAOYSA-L

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General description

Dibutyltin diacetate is an organotin compound that is commonly used as a catalyst in organic synthesis.

Application

Dibutyltin diacetate can be used as a catalyst to synthesize:
  • Wittenberger tetrazole derivatives by reacting with various nitriles in the presence of trimethylsilyl azide.
  • Carbamate derivatives from various isocyanates and alcohols in the presence of dichloromethane as solvent.
  • Urea derivatives from aryl isocyanates and various amines in the presence of 4-methylmorpholine.

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Muta. 2 - Repr. 1B - Skin Corr. 1B - Skin Sens. 1 - STOT RE 1 - STOT SE 1 Oral

Target Organs

thymus gland, thymus gland,Immune system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

302.9 °F - Pensky-Martens closed cup

Flash Point(C)

150.5 °C - Pensky-Martens closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Adrian Blaser et al.
Journal of medicinal chemistry, 55(1), 312-326 (2011-12-14)
Analogues of clinical tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824), in which the OCH(2) linkage was replaced with amide, carbamate, and urea functionality, were investigated as an alternative approach to address oxidative metabolism, reduce lipophilicity, and improve aqueous solubility. Several soluble monoaryl examples
T Noda et al.
Toxicology, 167(3), 181-189 (2001-10-02)
The present study was designed to assess changes in the teratogenic potency of di-n-butyltin diacetate (DBTA) with increasing maternal age in rats. Pregnant Wistar rats of 3, 7.5 or 12 months were treated orally with DBTA at 0, 7.5, 10
TMSN3-Bu2Sn (OAc) 2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
Yoneyama H, et al.
Tetrahedron Letters, 61, 151517-151517 (2020)
Critical gestational day of teratogenesis by di-n-butyltin diacetate in rats.
T Noda et al.
Bulletin of environmental contamination and toxicology, 49(5), 715-722 (1992-11-01)
Wenhua Chu et al.
Bioorganic & medicinal chemistry, 17(3), 1222-1231 (2009-01-03)
A series of N-substituted 9-azabicyclo[3.3.1]nonan-3alpha-yl phenylcarbamate analogs were synthesized. Among them, WC-26 and WC-59 were identified as the most potent sigma(2) receptor ligands (K(i)=2.58 and 0.82 nM, respectively) with high selectivity against sigma(1) (K(i) of sigma(1)/sigma(2) ratio=557 and 2087, respectively).
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