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10907

Sigma-Aldrich

Chloroacetaldehyde solution

produced by Wacker Chemie AG, Burghausen, Germany, ≥45.0% in H2O (density determination)

Synonym(s):

CLACH

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About This Item

Linear Formula:
ClCH2CHO
CAS Number:
107-20-0
Molecular Weight:
78.50
Beilstein/REAXYS Number:
1071226
EC Number:
203-472-8
MDL number:
MFCD00006992
UNSPSC Code:
12352100
PubChem Substance ID:
57646841
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

form

solid

concentration

≥45.0% in H2O (density determination)

bp

80-100 °C (lit.)

functional group

aldehyde
chloro

SMILES string

[H]C(=O)CCl

InChI

1S/C2H3ClO/c3-1-2-4/h2H,1H2

InChI key

QSKPIOLLBIHNAC-UHFFFAOYSA-N

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Application

Chloroacetaldehyde is a reagent used for converting adenine and its nucleoseides into fluorescent etheno derivatives which can be analysed by HPLC. It was used for derivatization in fluorometric determination of arprinocid and analogous compounds in human plasma .

Biochem/physiol Actions

Chloroacetaldehyde, a metabolite of ifosamide, influences oxidative phosphorylation in mitochondria. It causes breaking of DNA strands and strongly inhibits DNA synthesis.

Other Notes

prices for bulk quantities on request

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Aquatic Acute 1 - Carc. 2 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3454
BCCJ9066
BCCJ2999
BCCC9177
BCCD7290

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Preparation, titration, and storage of chloroacetaldehyde for fluorometric determination of adenine and its derivatives.
McCann WP, et al.
Analytical Chemistry, 55(8), 1454-1455 (1983)
Fluorogenic reaction between adenine derivatives and chloroacetaldehyde and its application to the determination of 9-(2-chloro-6-fluorobenzyl) adenine in human plasma.
Matuszewski BK and Bayne WF.
Analytica Chimica Acta, 227, 189-202 (1989)
Svenja K Brüggemann et al.
Cancer chemotherapy and pharmacology, 57(3), 349-356 (2005-09-01)
The ifosfamide metabolite chloroacetaldehyde had been made responsible for side effects only. We found in previous studies a strong cytotoxicity on human MX-1 tumor cells and xenografts in nude mice. Chloroacetaldehyde is supposed to act via alkylation or by inhibition
Stephanie L MacAllister et al.
Chemico-biological interactions, 202(1-3), 259-266 (2012-12-12)
Cyclophosphamide and ifosfamide are two commonly used DNA-alkylating agents in cancer chemotherapy that undergo biotransformation to several toxic and non-toxic metabolites, including acrolein and chloroacetaldehyde (CAA). Acrolein and CAA toxicities occur by several different mechanisms, including ROS formation and protein
Min Young Kim et al.
Chemical research in toxicology, 20(8), 1075-1083 (2007-07-31)
2-Chloroacetaldehyde (CAA), a metabolite of the carcinogen vinyl chloride, reacts with DNA to form cyclic etheno ()-lesions. AlkB, an iron-/alpha-ketoglutarate-dependent dioxygenase, repairs 1, N (6)-ethenodeoxyadenosine (A) and 3, N (4)-ethenodeoxycytidine (C) in site-specifically modified single-stranded viral genomes in vivo and
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