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248649

Sigma-Aldrich

Hydriodic acid

contains ≤1.5% hypophosphorous acid as stabilizer, ACS reagent, ≥47.0%

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Synonym(s):
Hydriotic acid
Empirical Formula (Hill Notation):
HI
CAS Number:
10034-85-2
Molecular Weight:
127.91
MDL number:
MFCD00011347
UNSPSC Code:
12352106
PubChem Substance ID:
329752753
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

form

liquid

contains

≤1.5% hypophosphorous acid as stabilizer

concentration

≥47.0%

bp

127 °C (lit.)

density

1.5 g/mL at 25 °C

anion traces

bromide, chloride (as Cl-): ≤0.05%
sulfate (SO42-): ≤0.005%

cation traces

Fe: ≤0.001%
heavy metals: ≤0.001%

storage temp.

2-8°C

SMILES string

I

InChI

1S/HI/h1H

InChI key

XMBWDFGMSWQBCA-UHFFFAOYSA-N

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Application

Hydriodic acid is a solution of hydrogen iodide in water. It is a strong acid. It is commonly used as a reagent in various reactions such as:
  • electrophilic hydriodination of alkenes and alkynes
  • cleavage of epoxides, ethers, and acetals; conversion of alcohols to iodides   
  • reducing agent for many groups including quinones, α-diketones, α-ketols, α-halo ketones, α-diazo ketones, and sulfoxides      
  • reductive cyclization of keto acids

Hydriodic acid (hypophosphorus acid as a stabilizer) can be used for the fabrication of benzylammonium hybrid layered metal-halide perovskites for spintronic and nonlinear optical applications

Pictograms

CorrosionEnvironment
GHS05,GHS09

Signal Word

Danger

Hazard Statements

H290,H314,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Siegfried Eigler et al.
Chemical communications (Cambridge, England), 49(67), 7391-7393 (2013-07-19)
The efficiency of reducing agents for the reduction of graphene oxide (GO) could be probed by scanning Raman spectroscopy. A film of graphene flakes derived from GO was probed to be graphene like. We also focus on the surface quality
Viscosities of aqueous hydrochloric acid solutions, and densities and viscosities of aqueous hydroiodic acid solutions.
Nishikata E, et al.
Journal of Chemical and Engineering Data, 26(3), 254-256 (1981)
Efficient reduction of polycyclic quinones, hydroquinones, and phenols with hydriodic acid.
Konieczny M and Harvey RG.
The Journal of Organic Chemistry, 44(26), 4813-4816 (1979)
Daniel J Weisenberger et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 24(3), 512-519 (2015-01-15)
The CpG island methylator phenotype (CIMP) represents a subset of colorectal cancers characterized by widespread aberrant DNA hypermethylation at select CpG islands. The risk factors and environmental exposures contributing to etiologic heterogeneity between CIMP and non-CIMP tumors are not known.
S Ito et al.
Pigment cell research, 11(2), 120-126 (1998-05-19)
Melanocytes produce two chemically distinct types of melanin pigments, eumelanins and pheomelanins. These pigments can be quantitatively analyzed by acidic KMnO4 oxidation or reductive hydrolysis with hydriodic acid (HI) to form pyrrole-2,3,5-tricarboxylic acid (PTCA) or aminohydroxyphenylalanine (AHP), respectively. Dark brown
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