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Basic Information

Molecular Structure:
CAS No.:	643-79-8
Name:	o-Phthalaldehyde
Article Data:	144
Cas Database

Formula:	C₈H₆O₂
Molecular Weight:	134.134
Synonyms:	1,2-Benzenedicarboxaldehyde;Phthalic dialdehyde;Phtalaldehydes [French];Phthalic aldehyde;o-Phthaldialdehyde;Phthalyldicarboxaldehyde;Benzene-1,2-dicarboxaldehyde;2-Phthalaldehyde;o-Phthaladlehyde;Phthalic dicarboxaldehyde;
EINECS:	211-402-2
Density:	1.189 g/cm³
Melting Point:	55-58 °C(lit.)
Boiling Point:	266.1 °C at 760 mmHg
Flash Point:	98.5 °C
Solubility:	Soluble in water
Appearance:	Light yellow powder
Hazard Symbols:	T, Xi, N
Risk Codes:	36/37/38-43-34-25-50
Safety:	26-28-36-45-36/37/39-61-37/39
Transport Information:	UN2923 8/PG 2
PSA:	34.14000
LogP:	1.31160

Synthetic route

: 612-14-6
phthalyl alcohol

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With bis(pyridine)silver(I) permanganate In benzene for 1h;	95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In neat (no solvent) at 20℃; for 2h; Milling;	86%
With tetrakis(pyridine)silver dichromate In benzene for 2h; Heating;	85%

: 59868-79-0
1,3-dihydroisobenzofuran-1-ol

: 524-38-9
N-hydroxyphthalimide

: 10102-43-9
nitrogen(II) oxide

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
In acetonitrile	95%

...Expand

: 496-14-0
1,3-dihydroisobenzofuran

: 524-38-9
N-hydroxyphthalimide

: 10102-43-9
nitrogen(II) oxide

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
In acetonitrile	94%

...Expand

: 1313208-32-0
C11H13NOS2

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 1h;	92%

: 13209-15-9
1,2-bis(dibromomethyl)benzene

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 1,2-bis(dibromomethyl)benzene With sulfuric acid Stage #2: With water; sodium hydrogencarbonate Product distribution / selectivity;	91%
With sulfuric acid Product distribution / selectivity;	79%
With sulfuric acid

: 612-14-6
phthalyl alcohol

A: 55479-94-2
2-(hydroxymethyl)benzaldehyde

B: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Product distribution; Heating; effect of various chromium(VI) based oxidants;	A 10% B 90%
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Heating;	A 10% B 90%
With cucurbit[8]uril; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water for 0.0833333h; Catalytic behavior; Reagent/catalyst; Temperature; Reflux;	A 76% B 7%

: 6500-54-5
1,2-bis-diacetoxymethyl-benzene

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With ethanol at 50 - 60℃; for 0.0833333h;	90%
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.25h; Irradiation;	86%
With N-sulfonic acid poly(4-vinylpyridinium) chloride In methanol at 20℃; for 0.583333h;	82%

: 88-95-9
Phthaloyl dichloride

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With 1 Product distribution; further reagent;	89%
With pentacoordinated hydrogenosilane 3 further reagent;	89%
With Cp2M(CO)H (M= Nb or Ta) In diethyl ether Yield given;
With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 120h; Yield given;

: 91-13-4
α,α'-dibromo-o-xylene

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With bis-{4-methoxy-phenyl}-selenoxyde; sodium hydrogencarbonate In acetonitrile at 75℃; for 5h;	84%
With air; sodium phenyltelluride 1.) THF, ethanol, reflux, 2 h, 2.) THF, ethanol, 25 deg C; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation 2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation View Scheme

: 24388-70-3
1,3-dihydro-1,3-dimethoxybenzo[c]furan

: 643-79-8
o-phthalic dicarboxaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrachloromethane; water Reflux;	81%
With sulfuric acid; water under 112.511 Torr; for 4h; pH=2.0; Purification / work up;	61.5%
With water; benzene-1,2-dicarboxylic acid at 20℃; for 48h;	95 % Chromat.

Raw Materials

95-47-6

141-78-6

108-86-1

135-19-3

Downstream Products

119-67-5

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Chemistry

Molecular Structure:

Molecular Formula: C₈H₆O₂
Molecular Weight: 134.132
IUPAC Name: Phthalaldehyde
Synonyms of Phthalaldehyde (CAS NO.643-79-8): 4-07-00-02138 (Beilstein Handbook Reference) ; BRN 0878317 ; EINECS 211-402-2 ; NSC 13394 ; Phtalaldehydes ; Phtalaldehydes [French] ; Phthalic aldehyde ; Phthalic dialdehyde ; Phthalyldicarboxaldehyde ; UNII-4P8QP9768A ; o-Phthalaldehyde ; o-Phthaldialdehyde ; 1,2-Benzenedicarboxaldehyde
CAS NO: 643-79-8
Classification Code: Anti-Infective Agents ; Disinfectants ; Enzyme inhibitors ; Indicators and reagents
Melting point: 55-58 °C
Polar Surface Area: 34.14 Å²
Index of Refraction: 1.622
Molar Refractivity: 39.75 cm³
Molar Volume: 112.7 cm³
Surface Tension: 48.3 dyne/cm
Density: 1.189 g/cm³
Flash Point: 98.5 °C
Enthalpy of Vaporization: 50.41 kJ/mol
Boiling Point: 266.1 °C at 760 mmHg
Vapour Pressure: 0.0088 mmHg at 25°C
Form: powder
Color: yellow
Water: Solubility soluble
Sensitive: Air Sensitive
Merck: 7368
BRN: 878317
Stability: Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.

Uses

Phthalaldehyde (CAS NO.643-79-8) is pharmaceutical intermediate, and it is used in pharmaceutical inspection. It is mainly used in medicine, dyestuff, etc. It is commonly used as a high-level disinfectant for medical instruments.

Production

There are two synthesis method of Phthalaldehyde (CAS NO.643-79-8): the first described in 1887 when it was prepared from α,α,α',α’-tetrachloro-ortho-xylene. And the second that hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	unreported	7mg/kg (7mg/kg)		Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 246, Pg. 851, 1958.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by an unspecified route. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Hazard Codes of Phthalaldehyde (CAS NO.643-79-8): Xi,T,N
Risk Statements: 36/37/38-43-34-25-50
36/37/38: Irritating to eyes, respiratory system and skin
43: May cause sensitization by skin contact
34: Causes burns
25: Toxic if swallowed
50: Very Toxic to aquatic organisms
Safety Statements: 26-28-36-45-36/37/39-61-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
61: Avoid release to the environment. Refer to special instructions safety data sheet
37/39: Wear suitable gloves and eye/face protection
RIDADR: UN2923 8/PG 2
WGK Germany: 3
RTECS: TH6950000
F: 1-8-10: Sensitive to air and humidity. Photosensitive. Keep under argon.
Hazard Note: Irritant/Air Sensitive
HS Code: 29122900

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